Methanol → 2-(1,1-Difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine

HRID 1435544Notes

Reaction equation

[F:1][C:2]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21]C(=O)C)=[CH:20][C:7]=2[N:6]=1)([F:4])[CH3:3].[OH-].[Na+].CO>O>[F:4][C:2]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:8]2[CH:17]=[CH:18][C:19]([NH2:21])=[CH:20][C:7]=2[N:6]=1)([F:1])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N-[2-(1,1-difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]acetamide (1.07 g, 3.17 mmol), 6 M aqueous solution of NaOH (5 mL) and MeOH (5 mL) was heated to 70° C. for 24 h. The reaction mixture was diluted with water (200 mL) and the product was extracted with EtOAc (4×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was concentrated to provide the title compound as white solid. Yield: 0.90 g (96%); MS (ESI) (M+H)+=296.2.

Workup

extractionthe product was extracted with EtOAc (4×100 mL)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationthe solvent was concentrated

Sources & evidence

ORD record: ord-536d5f219e804575b16016c3dedff495
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615642B2

Reaction notes

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