(8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide

Base Information

• Chemical Name: (8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide
• CAS No.: 957118-49-9
• Molecular Formula: C₃₁H₂₉F₂N₅O₃
• Molecular Weight: 557.6
• Mol file: 957118-49-9.mol

Synonyms:(8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide;

Chemical Property of (8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide

Chemical Property:

• Boiling Point: 812.099 °C at 760 mmHg
• Flash Point: 444.942 °C
• PSA: 106.92000
• Density: 1.45 g/cm³
• LogP: 4.19770
• Solubility.: Soluble in DMSO

Purity/Quality:

98% min ^*data from raw suppliers

MK-3207 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: MK-3207 is a potent and orally active calcitonin gene-related peptide (CGRP) receptor antagonist used for the treatment of migraine.

Technology Process of (8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide

There total 35 articles about (8R)-8-(3,5-Difluorophenyl)-10-oxo-N-[(2R)-1,1',2',3-tetrahydro-2'-oxospiro[2H-indene-2,3'-[3H]pyrrolo[2,3-b]pyridin]-5-yl]-6,9-diazaspiro[4.5]decane-9-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(R)-5-amino-1,3-dihydrospiro[indene-2,3’-pyrrolo[2,3-b]pyridin]-2’(1’H)-one (957130-49-3) + C16H18F2N2O3 (957187-34-7) → [3H]-MK 3207 (957118-49-9)

Guidance literature:

(R)-5-amino-1,3-dihydrospiro[indene-2,3’-pyrrolo[2,3-b]pyridin]-2’(1’H)-one; C₁₆H₁₈F₂N₂O₃; With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 17 - 20 ℃; for 0.5h; Industry scale; Inert atmosphere;

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 14 - 23 ℃; for 39.5h; Industry scale; Inert atmosphere;

Reference yield:

C36H37F2N5O5 → [3H]-MK 3207 (957118-49-9)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 0 ℃;

DOI:10.1021/ml900016y

Reference yield:

cycloleucine methyl ester hydrochloride (60421-23-0) → [3H]-MK 3207 (957118-49-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium phosphate / N,N-dimethyl-formamide / -15 - 5 °C / Industry scale; Inert atmosphere

1.2: Industry scale; Inert atmosphere

2.1: hydrogen; methanesulfonic acid / ((-)-(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride / methanol / 18 h / 80 °C / 20686.5 Torr / Industry scale

3.1: N-ethyl-N,N-diisopropylamine / methanol / pH 6 / Industry scale

4.1: thionyl chloride; N-ethyl-N,N-diisopropylamine / toluene / -35 - -20 °C / Industry scale

5.1: sodium periodate / toluene; acetonitrile; water / 15 - 25 °C / Aqueous phosphate buffer; Industry scale

6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; acetonitrile / 20 °C / Industry scale

6.2: 70 °C / Industry scale

6.3: pH 8 / Industry scale

7.1: water; lithium hydroxide / tetrahydrofuran / 2 h / 10 °C

7.2: 0 °C / pH < 1

7.3: 85 °C

8.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 17 - 20 °C / Industry scale; Inert atmosphere

8.2: 39.5 h / 14 - 23 °C / Industry scale; Inert atmosphere

With potassium phosphate; sodium periodate; thionyl chloride; methanesulfonic acid; water; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; lithium hydroxide; ((-)-(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

3,5-difluorobromobenzene

2-bromo-1-(3,5-difluorophenyl)ethanone

cycloleucine methyl ester hydrochloride

4-amino-phthalic acid dimethyl ester

Refernces

• 1、 Bell, Ian M.,Gallicchio, Steven N.,Wood, Michael R.,Quigley, Amy G.,Stump, Craig A.,Zartman, C. Blair,Fay, John F.,Li, Chi-Chung,Lynch, Joseph J.,Moore, Eric L.,Mosser, Scott D.,Prueksaritanont, Thomayant,Regan, Christopher P.,Roller, Shane,Salvatore, Christopher A.,Kane, Stefanie A.,Vacca, Joseph P.,Selnick, Harold G.. "Discovery of MK-3207: A highly potent, orally bioavailable CGRP receptor antagonist". scheme or table. p. 24 - 29. Retrieved 2010/11/04.