Phenol → HCID 66835893, compound

HRID 2404455Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([C:31]3[NH:35][C:34]4[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=4[N:32]=3)[O:23][CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C1(O)C=CC=CC=1.Cl[Si](C)(C)C>ClCCCl>[CH3:30][N:27]1[CH2:26][CH2:25][CH:24]([O:23][CH:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:15]#[C:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:17]=2)[C:31]2[NH:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)-methyl]phenylethynyl}piperidine-1-carboxylic acid tert-butyl ester (160 mg) in 1,2-dichloroethane (10 mL) are added phenol (940 mg) and chlorotrimethylsilane (1.26 mL). The reaction mixture is heated to 100° C. for 30 minutes. Volatiles are removed under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 85/15/1.5) to afford 2-[(1-methylpiperidin-4-yloxy)(3-piperidin-4-ylethynyl-phenyl)methyl]-1H-benzimidazole.

Workup

customVolatiles are removed under reduced pressure
customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 85/15/1.5)

Sources & evidence

ORD record: ord-1c16ab0efcde40a69266c8ea5b8e2b5c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802664B2

Reaction notes

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