4-bromo-N-cyclopropyl-2-fluorobenzamide → Isopropyl 4-{5-[4-(cyclopropylcarbamoyl)-3-fluorophenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710168Notes

Reaction equation

HRID 710168 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:29]=2)O1.Br[C:32]1[CH:43]=[CH:42][C:35]([C:36]([NH:38][CH:39]2[CH2:41][CH2:40]2)=[O:37])=[C:34]([F:44])[CH:33]=1>>[CH:39]1([NH:38][C:36]([C:35]2[CH:42]=[CH:43][C:32]([C:9]3[CH:10]=[CH:11][C:12]4[O:16][C:15]([CH:17]5[CH2:18][CH2:19][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]5)=[N:14][C:13]=4[CH:29]=3)=[CH:33][C:34]=2[F:44])=[O:37])[CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 90800384-bromo-N-cyclopropyl-2-fluorobenzamideHCID 71090092Isopropyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71257268Isopropyl 4-{5-[4-(cyclopropylcarbamoyl)-3-fluorophenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 7%

Procedure

Following the General Procedure-3, the titled compound (20 mg) was prepared from Intermediate 14 (250 mg, 0.61 mmol) and 4-bromo-N-cyclopropyl-2-fluorobenzamide (156 mg, 0.61 mmol) as an off-white solid. M.P.: 162-165° C. MS (m/z): 466.3 [M+H]+.

Sources & evidence

ORD record
ord-2163f132f545410ebb4507cac6aa17de
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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