Ammonium Chloride → HCID 23145758, compound

HRID 13361Notes

Reaction equation

[CH3:1][Li].[C:3]([C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[C:14]([CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3[C:33](=[O:35])[CH3:34])=[CH:15][C:16]3[NH:20][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:18][C:17]=3[CH:27]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1>[OH:5][C:3]([C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[C:14]([CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3[C:33](=[O:35])[CH3:34])=[CH:15][C:16]3[NH:20][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[N:18][C:17]=3[CH:27]=2)=[CH:8][CH:7]=1)([CH3:1])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

0.1 ml of methyl lithium (1.0 M diethyl ether solution) was added to a tetrahydrofuran (1.5 ml) solution of 15.0 mg of 1-(2-(6-(6-acetyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone obtained in Example 341, at −78° C., and the reaction liquid was stirred at −78° C. for 30 minutes. The reaction liquid was poured into aqueous saturated ammonium chloride solution, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=7.5/1) to obtain the entitled compound as a yellow solid.

Workup

customthe reaction liquid
customThe reaction liquid
extractionextracted with chloroform
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=7.5/1)

Sources & evidence

ORD record: ord-ac276c02415f4120b9ae0adc43d64e7f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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