Tributylamine → HCID 178433855, compound

HRID 68705Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[NH:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27](O)=[O:28])=[CH:26][C:21]=2[N:20]=[CH:19]1.N(CCCC)(CCCC)CCCC.[I-].ClC1C=CC=C[N+]=1C>CN(C)C=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:27]([C:25]3[CH:24]=[CH:23][C:22]4[NH:18][CH:19]=[N:20][C:21]=4[CH:26]=3)=[O:28])=[CH:8][CH:9]=2)[N:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 3-methyl-1-phenyl-1H-indazol-6-amine (520 mg, 2.33 mmol, 1.00 equiv) in N,N-dimethylformamide (50 mL), 1H-benzo[d]imidazole-5-carboxylic acid (324 mg, 2.00 mmol, 0.86 equiv), NBu3 (925 mg, 5.00 mmol, 2.14 equiv). To the resulting mixture was then added 2-chloro-1-methylpyridiniumiodide (612 mg, 2.40 mmol, 1.03 equiv) at 50° C. The resulting solution was stirred for 2 days at 100° C. in an oil bath, then concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (50:1). The resulting mixture was washed with methanol (1×10 mL) and diethyl ether (1×10 mL) to yield N-(3-methyl-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
customat 50° C
concentrationconcentrated under vacuum
washThe resulting mixture was washed with methanol (1×10 mL) and diethyl ether (1×10 mL)

Sources & evidence

ORD record: ord-b4ecc53f68484d5dab5799e6cd2fdb4d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822447B2

Reaction notes

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