7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester

Base Information

• Chemical Name: 7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester
• CAS No.: 561297-88-9
• Molecular Formula: C14H20N2O2
• Molecular Weight: 274.363
• Mol file: 561297-88-9.mol

Synonyms:7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester;tert-Butyl 7'-amino-1'h-spiro[cyclopropane-1,4'-isoquinoline]-2'(3'h)-carboxylate;tert-butyl N-[7-amino-4-spiro-1'-cyclopropane-3,4-dihydro-1H-isoquinoline]-2-carbamate

Chemical Property of 7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester

Chemical Property:

• PSA: 55.56000
• LogP: 3.57020

Purity/Quality:

NLT 98% ^*data from raw suppliers

7’-Aminospiro[cyclopropane-1,4’(1’H)-isoquinoline]-2’(3’H)carboxylicAcid1,1-DimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7’-Aminospiro[cyclopropane-1,4’(1’H)-isoquinoline]-2’(3’H)carboxylic Acid 1,1-Dimethyl Ester is used in the synthesis of wee-1 kinase inhibitors for cancer therapy.

Technology Process of 7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester

There total 9 articles about 7'-AMinospiro[cyclopropane-1,4'(1'H)-isoquinoline]-2'(3'H)carboxylic Acid 1,1-DiMethyl Ester 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: 93.0%

tert-butyl 7’-nitro-1‘H-spiro[cyclopropane-1,4’-isoquinoline]-2’(3’H)-carboxylate (618446-27-8) → tert-butyl 7′-amino-1′H-spiro[cyclopropane-1,4′-isoquinoline]-2′(3′H)-carboxylate (561297-88-9)

Guidance literature:

With ammonium chloride; tin(ll) chloride; In ethanol; at 70 ℃; for 1h;

Reference yield:

7′-nitro-1’H-spiro [cyclopropane-1,4’-isoquinoline]-3’(2’H)-one (1092794-09-6) → tert-butyl 7′-amino-1′H-spiro[cyclopropane-1,4′-isoquinoline]-2′(3′H)-carboxylate (561297-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 2 h / Reflux

1.2: 1 h / Reflux

2.1: sodium hydroxide / water; 1,4-dioxane / 0.08 h / 0 °C

2.2: 2 h / 0 - 20 °C

3.1: tin(ll) chloride; ammonium chloride / ethanol / 1 h / 70 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; ammonium chloride; tin(ll) chloride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

Reference yield:

1′H-spiro[cyclopropane-1,4’-isoquinoline]-3’(2’H)-one (1092794-08-5) → tert-butyl 7′-amino-1′H-spiro[cyclopropane-1,4′-isoquinoline]-2′(3′H)-carboxylate (561297-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium nitrate; sulfuric acid / 0.17 h

2.1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 2 h / Reflux

2.2: 1 h / Reflux

3.1: sodium hydroxide / water; 1,4-dioxane / 0.08 h / 0 °C

3.2: 2 h / 0 - 20 °C

4.1: tin(ll) chloride; ammonium chloride / ethanol / 1 h / 70 °C

With sodium tetrahydroborate; sulfuric acid; boron trifluoride diethyl etherate; ammonium chloride; potassium nitrate; tin(ll) chloride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

upstream raw materials:

tert-butyl 7’-nitro-1‘H-spiro[cyclopropane-1,4’-isoquinoline]-2’(3’H)-carboxylate

7′-nitro-1’H-spiro [cyclopropane-1,4’-isoquinoline]-3’(2’H)-one

1′H-spiro[cyclopropane-1,4’-isoquinoline]-3’(2’H)-one

7’-nitro-2’,3’-dihydro-1’H-spiro[cyclopropane-1,4’-isoquinoline]

Downstream raw materials:

6-(2,6-dichlorophenyl)-2-(2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-isoquinolin]-7'-ylamino)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

6-(2,6-dichlorophenyl)-2-{[2'-(methylsulfonyl)-2',3'-dihydro-1'H-spiro[cyclopropane-1,4'-isoquinolin]-7'-yl]amino}imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

tert-butyl 7'-{[6-(2,6-dichlorophenyl)-5-oxo-5,6-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-2-yl]amino}-1'H-spiro[cyclopropane-1,4'-isoquinoline]-2'(3'H)-carboxylate

tert-butyl 7'-({5-oxo-6-[4-(prop-2-en-1-yloxy)phenyl]-5,6-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-2-yl}amino)-1'H-spiro[cyclopropane-1,4'-isoquinoline]-2'(3'H)-carboxylate

Refernces

• 1、 -. "SUBSTITUTED L,2-DIHYDRO-3H-PYRAZOLO[3,4-D]PYRIMIDIN-3-ONES". Paragraph 0239. . Retrieved 2019/10/01.