Methyl acetoacetate → 2-[5-(5-Chloro-2-fluoro-phenyl)-3-cyclohexylcarbamoyl-2-methyl-pyrrol-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 229872Notes

Reaction equation

CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[F:20])=O.[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@@H:29]1[CH2:33][NH2:34])=[O:27])([CH3:24])([CH3:23])[CH3:22].[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][N:34]1[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:10][C:4]([C:3](=[O:8])[NH:41][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:5]1[CH3:6])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 7965Cyclohexylamine

HCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate

HCID 790219212-Bromo-1-(5-chloro-2-fluorophenyl)ethanone

Product 1

HCID 116920862-[5-(5-Chloro-2-fluoro-phenyl)-3-cyclohexylcarbamoyl-2-methyl-pyrrol-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-fluoro-5-chlorophenyl]-ethanone as compound of formula S, (R)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 518.3 (M+H)+.

Sources & evidence

ORD record: ord-67035d2272a7413bb78c3ff9a6709651
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563910B2

Reaction notes

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