Dimethylformamide → 5-benzyloxy-6-(2-fluorophenoxy)-2-pyrazin-2-yl-1H-benzimidazole

HRID 13327Notes

Reaction equation

O.O.[Sn](Cl)Cl.CN(C)C=O.[CH2:11]([O:18][C:19]1[C:24]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[CH:23][C:22]([NH:33][C:34]([C:36]2[CH:41]=[N:40][CH:39]=[CH:38][N:37]=2)=O)=[C:21]([N+:42]([O-])=O)[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[CH2:11]([O:18][C:19]1[C:24]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[CH:23][C:22]2[NH:33][C:34]([C:36]3[CH:41]=[N:40][CH:39]=[CH:38][N:37]=3)=[N:42][C:21]=2[CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3.72 g of tin(II) chloride dihydrate was added to a dimethylformamide (16 ml) suspension of 1.52 g of N-(4-benzyloxy-5-(2-fluorophenoxy)-2-nitrophenyl)pyrazinecarboxamide, and the reaction liquid was stirred overnight at 80° C. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was washed with a mixed solvent of ethyl acetate and hexane to obtain the entitled compound as a yellow solid.

Workup

customthe reaction liquid
customThe reaction liquid
washwashed with aqueous saturated sodium bicarbonate, water and saturated saline in order
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure
washthe resulting residue was washed with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record: ord-2f53b352f3654eb7b81ad112302344a4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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