Trifluoroacetic acid → (RS)-5,6-difluoro-1-methyl-2-piperidin-2-ylmethyl-1H-benzoimidazole

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]1[N:19]([CH3:20])[C:18]2[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:17]=2[N:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[F:25][C:23]1[C:22]([F:26])=[CH:21][C:18]2[N:19]([CH3:20])[C:15]([CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[N:16][C:17]=2[CH:24]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66968213(RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23146341(RS)-5,6-difluoro-1-methyl-2-piperidin-2-ylmethyl-1H-benzoimidazole

Procedure

(RS)-2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester, D60 (0.5 g) was treated with trifluoroacetic acid (5 ml) as described for Description 6 to afford the title compound (0.363 g)

Sources & evidence

ORD record: ord-b02f8042ea544e779ded9dc36fc151f7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928124B2

Reaction notes

Loading…