Tributylamine → HCID 178437917, compound

HRID 68695

Reaction equation

Cl.[CH2:2]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=1)[CH3:3].C(N(CCCC)CCCC)CCC.[NH:33]1[C:37]2[CH:38]=[CH:39][C:40]([C:42](O)=[O:43])=[CH:41][C:36]=2[N:35]=[CH:34]1.[I-].ClC1C=CC=C[N+]=1C>CN(C)C=O>[CH2:2]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:42]([C:40]3[CH:39]=[CH:38][C:37]4[NH:33][CH:34]=[N:35][C:36]=4[CH:41]=3)=[O:43])=[CH:10][CH:11]=2)[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=1)[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 3-ethyl-1-phenyl-1H-indazol-6-amine hydrochloride (300 mg, 1.10 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL), tributylamine (492 mg, 2.66 mmol, 2.50 equiv), 1H-benzo[d]imidazole-5-carboxylic acid (180 mg, 1.11 mmol, 1.00 equiv), 2-chloro-1-methylpyridinium iodide (330 mg, 1.29 mmol, 1.20 equiv). The resulting solution was stirred for 2 days at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (50:1). The resulting mixture was diluted with methanol (10 mL) and the solids were washed with diethyl ether (1×50 mL) to yield N-(3-ethyl-1-phenyl-1H-indazol-6-yl)-1H-benzo[d]imidazole-5-carboxamide as a yellow solid.

Workup

customInto a 100-mL 3-necked round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
additionThe resulting mixture was diluted with methanol (10 mL)
washthe solids were washed with diethyl ether (1×50 mL)

Sources & evidence

ORD record: ord-29a404dda10f4116845058069a887d7a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822447B2

Linked notes

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