Formic Acid → HCID 46852044, compound

HRID 241667Notes

Reaction equation

[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@H:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].C=O.[CH:30](O)=O>O1CCOCC1>[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@H:17]3[CH2:21][CH2:20][N:19]([CH3:30])[CH2:18]3)(=[O:15])=[O:16])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:22][C:23]([CH3:24])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

To solution of (S)—N,N-dimethyl-2-(2-neopentyl-5-(pyrrolidin-3-ylsulfonyl)-1H-benzo[d]imidazol-1-yl)ethanamine (STEP F, 776 mg, 1.98 mmol) in 1,4-dioxane (5 mL) were added 37% formalin (588 microL, 7.31 mmol) and formic acid (379 microL, 9.88 mmol). The mixture was stirred at 60° C. for 1 h. The mixture was concentrated in vacuo. The residue was diluted with saturated sodium bicarbonate aqueous solution (4 mL) and extracted with ethyl acetate (60 mL×2). The combined organic layers were washed with brine and dried over sodium sulfate. The resulting solution was concentrated in vacuo and residue was purified by amine gel column chromatography (dichloromethane-ethyl acetate, gradient) to give the title compound (704 mg, 87%) as clear grease.

Workup

concentrationThe mixture was concentrated in vacuo
additionThe residue was diluted with saturated sodium bicarbonate aqueous solution (4 mL)
extractionextracted with ethyl acetate (60 mL×2)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationThe resulting solution was concentrated in vacuo and residue
customwas purified by amine gel column chromatography (dichloromethane-ethyl acetate, gradient)

Sources & evidence

ORD record: ord-d38302ee6c384b75af479c9b94e874ce
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653063B2

Reaction notes

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