4-Nitrophenyl chloroformate → HCID 178480742, compound

HRID 2236672Notes

Reaction equation

HRID 2236672 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31]>CN(C)C(=O)C>[N+:39]([C:36]1[CH:35]=[CH:34][C:33]([O:32][C:30](=[O:31])[NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]3=[CH:14][NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)=[CH:38][CH:37]=1)([O-:41])=[O:40]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 178480741HCID 178480741, compound

Product 1

HCID 178480742HCID 178480742, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

An amount of 200 mg (0.53 mmol) of (4Z)-6-amino-4-({[4-(4-methylpiperazin-1-yl)phenyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione and 4-nitrophenyl chloroformate 320.0 mg (1.59 mmol) is stirred in N,N-dimethylacetamide at 100° C. for 1 hour. After cooling, the solvent is evaporated and stirred in 3 mL of water for 10 minutes. The solid precipitate is collected with ether to give 180 mg (70% yield) of (4-{[4(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-1,3-dioxo-1,2,3,4-tetrahyro-isoquinolin-6-yl)-carbamic acid 4-nitro-phenyl ester.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated
  3. customThe solid precipitate is collected with ether

Sources & evidence

ORD record
ord-9c92c35f4d564f5992a703877ac45c60
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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