{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester → 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-4-methoxy-1-[(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-pyrrolidin-3-yl}-amide
Reaction equation
C(O[C:4](=[O:22])[CH2:5][N:6]1[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:7]1)C.[CH3:23][CH:24]1[CH2:29][CH2:28][C:27]2[S:30][C:31]([NH2:33])=[N:32][C:26]=2[NH:25]1>>[CH3:12][O:11][C@H:9]1[CH2:10][N:6]([CH2:5][C:4](=[O:22])[NH:33][C:31]2[S:30][C:27]3[CH2:28][CH2:29][CH:24]([CH3:23])[NH:25][C:26]=3[N:32]=2)[CH2:7][C@@H:8]1[NH:13][C:14]([C:16]1[S:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:15]Participants
3
Reactant 2
Product 1
Procedure
In analogy to example 25.3 {(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester (example 25.2) was reacted with 5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylamine (CAS 17899-48-8) to give 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-4-methoxy-1-[(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-pyrrolidin-3-yl}-amide as yellow solid. MS 470.5 ([M+H]+)
Sources & evidence
- ORD record
- ord-e9263720d071436c8b1e96d99da13669
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820699B2
Reaction notes
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