Diisopropylethylamine → N-{4-Chloro-3-[6-chloro-5-(3,3-difluoropyrrolidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-2,2-dimethyl-propionamide

HRID 1258637Notes

Reaction equation

HRID 1258637 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH2:18])[C:7]([NH2:17])=[CH:8][C:9]=1[N:10]1[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11]1.[Cl:19][C:20]1[CH:33]=[CH:32][C:23]([CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:22][C:21]=1[N:34]=[C:35]=S.CCN(C(C)C)C(C)C>CC#N>[Cl:19][C:20]1[CH:33]=[CH:32][C:23]([CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:22][C:21]=1[NH:34][C:35]1[NH:18][C:6]2[CH:5]=[C:4]([Cl:3])[C:9]([N:10]3[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11]3)=[CH:8][C:7]=2[N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 679580194-Chloro-5-(3,3-difluoropyrrolidin-1-yl)benzene-1,2-diamine dihydrochlorideHCID 86646343HCID 86646343, compound

Product 1

HCID 67975174N-{4-Chloro-3-[6-chloro-5-(3,3-difluoropyrrolidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-5-(3,3-difluoropyrrolidin-1-yl)benzene-1,2-diamine dihydrochloride (340 mg, 1.1 mmol) was added to N-(4-chloro-3-isothiocyanatobenzyl)-2,2-dimethyl-propionamide (300 mg, 1.1 mmol) in MeCN (10 mL) and stirred at rt overnight. After addition of DIPEA (0.41 μL, 2.3 mmol) the reaction mixture was stirred at rt for 4.5 h. The mixture was concentrated. The crude was purified by chromatography to give the sub-title compound.

Workup

  1. stirringwas stirred at rt for 4.5 h
  2. concentrationThe mixture was concentrated
  3. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-4eb431c42b41453b98e0e184db763666
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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