Water → N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

HRID 468724Notes

Reaction equation

HRID 468724 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH2:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:16]([CH:13]3[CH2:15][CH2:14]3)=[O:17])[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 529877577-Bromoisoquinolin-3-amine

Product 1

HCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamideYield 80.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold solution (below 0° C.) of 7-bromoisoquinolin-3-amine (20 g, 0.09 mol) in pyridine (150 mL) was added cyclopropanecarbonyl chloride (11.2 g, 0.108 mol) dropwise. The mixture was stirred at room temperature overnight. After water (500 mL) was added, the reaction mixture was stirred for 30 min. Solid was collected by filtration and washed with water to give the desired product (21 g, 80.4%). LCMS (ESI): RT (min)=1.009, M+H+=290.7, method=A. 1H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1H), 9.10 (s, 1H), 8.44 (s, 1H), 8.30 (s, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H), 2.02-2.10 (m, 1H), 0.84-0.79 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred for 30 min
  2. filtrationSolid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-4d95b0387d644754963a2f79b493ec66
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

Loading…