4-Chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine → HCID 178483242, compound

HRID 1258658Notes

Reaction equation

HRID 1258658 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N:16]=[C:17]=S)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:22]=[C:23]([NH2:37])[C:24]([NH2:36])=[CH:25][C:26]=1[N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][N:33]([CH3:35])[CH3:34]>CN(C=O)C>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH:16][C:17]2[NH:36][C:24]3[CH:25]=[C:26]([N:27]4[CH2:31][CH2:30][CH2:29][CH:28]4[CH2:32][N:33]([CH3:35])[CH3:34])[C:21]([Cl:20])=[CH:22][C:23]=3[N:37]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 679577624-Chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamineHCID 86646335tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

Product 1

HCID 178483242HCID 178483242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Chloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester (68 mg, 0.2 mmol) followed by TEA (160 μL, 1.2 mmol) were added to 4-chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine (95 mg) in DMF (3 mL). The mixture was stirred at rt for 4 h and then purified by chromatography to give the sub-title compound.

Workup

  1. custompurified by chromatography

Sources & evidence

ORD record
ord-9a40ec4ec65b4c0192e74f4338b6d80d
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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