Cyclopropylamine → N-cyclopropyl-4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzamide

HRID 1051181Notes

Reaction equation

HRID 1051181 reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][NH:4][C:5]1[C:13]2[N:12]=[CH:11][N:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.CN(C(ON1N=NC2[CH:35]=[CH:36][CH:37]=[N:38]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>C1COCC1>[CH:37]1([NH:38][C:18](=[O:20])[C:17]2[CH:16]=[CH:15][C:14]([N:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([NH:4][CH2:3][CH:2]([CH3:23])[CH3:1])[C:13]=4[N:12]=[CH:11]3)=[CH:22][CH:21]=2)[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 683865474-[4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl]Benzoic acid

Product 1

HCID 66563616N-cyclopropyl-4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzoic acid (63 mg, 0.2 mmol) which was prepared according to intermediate example 4-1 in THF (5 mL), at rt was added HATU (85 mg, 0.22 mmol), DIPEA (29 mg, 0.22 mmol) and cyclopropylamine (12.8 mg, 0.22 mg) in one portion. After stirring for 4 h, the solution was evaporated and the remaining solid was purified by flash chromatography to yield N-cyclopropyl-4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzamide as an off-white solid (24 mg, 33.8%).

Workup

  1. customthe solution was evaporated
  2. customthe remaining solid was purified by flash chromatography

Sources & evidence

ORD record
ord-9ee03fa2b16c4ba7bbe8bfe604b8f33d
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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