Diisopropylcarbodiimide → HCID 178483275, compound

HRID 1258639Notes

Reaction equation

HRID 1258639 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][CH:29]([CH2:32][N:33]([CH3:35])[CH3:34])[CH2:28]1.CC(C)N=C=NC(C)C>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][CH:29]([CH2:32][N:33]([CH3:35])[CH3:34])[CH2:28]4)[C:21]([Cl:20])=[CH:22][C:23]=3[N:37]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679579304-Chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamineHCID 86646335tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

Product 1

HCID 178483275HCID 178483275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Chloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester (111 mg, 0.4 mmol) was added to 4-chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine (100 mg, 0.4 mmol) in DMF (3 mL). The mixture was stirred at rt overnight, DIC (62.4 μL, 0.4 mmol) was added and stirring was continued at 80° C. for 3 h. The mixture was concentrated and the crude was purified by chromatography to give the sub-title compound.

Workup

  1. stirringstirring
  2. waitwas continued at 80° C. for 3 h
  3. concentrationThe mixture was concentrated
  4. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-da32a1357ad74a7a9a307a2455ecdf65
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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