1-(4-Amino-3-fluorophenyl)pyridin-2-one → 5-chloro-thiophene-2-carboxylic acid ((R)-1-{1-[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-ethyl}-pyrrolidin-3-yl)-amide

HRID 1162612Notes

Reaction equation

HRID 1162612 reaction equation
C(O[C:4](=[O:21])[CH:5]([N:7]1[CH2:11][CH2:10][C@@H:9]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[CH2:8]1)[CH3:6])C.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=[O:35])=[CH:25][C:24]=1[F:36]>>[F:36][C:24]1[CH:25]=[C:26]([N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=[O:35])[CH:27]=[CH:28][C:23]=1[NH:22][C:4]([CH:5]([N:7]1[CH2:11][CH2:10][C@@H:9]([NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[CH2:8]1)[CH3:6])=[O:21]

Participants

3

Reactant 2

HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-oneHCID 587482892-{(R)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidin-1-yl}-propionic acid ethyl ester

Product 1

HCID 587483435-chloro-thiophene-2-carboxylic acid ((R)-1-{1-[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-ethyl}-pyrrolidin-3-yl)-amide

Procedure

6.4 Using general procedure F 2-{(R)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidin-1-yl}-propionic acid ethyl ester was reacted with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (CAS 536747-52-1, prepared according to WO 2003045912) to give 5-chloro-thiophene-2-carboxylic acid ((R)-1-{1-[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-ethyl}-pyrrolidin-3-yl)-amide. Yellow solid. MS 487.4 ([M−H]−)

Sources & evidence

ORD record
ord-16fb5fc165ed4d28bb8077d445fd63f7
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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