Acetic Acid → HCID 57611030, compound

HRID 709358Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([C@@H:13]2[CH2:17][C:16]([F:19])([F:18])[CH2:15][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=O)=[CH:4][CH:3]=1.C(O)(=O)C.C(O)(=O)C.[NH3:36].C1(C)C(C)=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:36][C:11]([C@@H:13]3[CH2:17][C:16]([F:19])([F:18])[CH2:15][N:14]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

In a 50 mL seal tube, (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-4,4-difluoropyrrolidine-1-carboxylate (1.8 g, 4.02 mmol) and acetic acid, ammonia acetate salt (1.55 g, 20.1 mmol) were combined with xylene (16 ml). The reaction mixture was heated to 140° C. and stirred for 4 hr. The reaction mixture was cooled and diluted with EtOAc (50 ml). It was washed with water and brine, dried with MgSO4, concentrated and purified on a silica gel column (CH2Cl2, 30%, 50%, 80% EtOAc/CH2Cl2) to afford (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4,4-difluoropyrrolidine-1-carboxylate as a yellow solid (1.77 g, 74%): ESI-LRMS m/e calcd for C18H22BrF2N3O2 [M+] 428. found 429 [M+H+].

Workup

customIn a 50 mL seal tube
temperatureThe reaction mixture was cooled
washIt was washed with water and brine
dry with materialdried with MgSO4
concentrationconcentrated
custompurified on a silica gel column (CH2Cl2, 30%, 50%, 80% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-8bf8f2abd84541d795828cc9dc807833
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180193B2

Reaction notes

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