4-(3-Fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester → 4-(3-Fluoro-benzyl)-7-[4-(5-fluoro-thiophene-2-carbonyl)-piperazin-1-yl]-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester
Reaction equation
C(OC(C1C(=O)N(CC2C=CC=C(F)C=2)C2C=CSC=2C=1N1CCNCC1)=O)C.[CH:30]([O:33][C:34]([C:36]1[C:41](=[O:42])[N:40]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=2)[C:39]2[CH:51]=[CH:52][S:53][C:38]=2[C:37]=1[N:54]1[CH2:59][CH2:58][N:57]([C:60]([C:62]2[S:63][C:64]([F:67])=[CH:65][CH:66]=2)=[O:61])[CH2:56][CH2:55]1)=[O:35])(C)[CH3:31]>>[CH2:30]([O:33][C:34]([C:36]1[C:41](=[O:42])[N:40]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=2)[C:39]2[CH:51]=[CH:52][S:53][C:38]=2[C:37]=1[N:54]1[CH2:55][CH2:56][N:57]([C:60]([C:62]2[S:63][C:64]([F:67])=[CH:65][CH:66]=2)=[O:61])[CH2:58][CH2:59]1)=[O:35])[CH3:31]Participants
3
Reactant 2
Product 1
Procedure
This compound was prepared from 4-(3-fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (19) by applying the same procedure as described for 4-(3-fluoro-benzyl)-7-[4-(5-fluoro-thiophene-2-carbonyl)-piperazin-1-yl]-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid isopropyl ester (21). Yield 2.22 g (85%). 1H-NMR (DMSO-d6) δ 1.29 (t, J=7.2 Hz, 3H), 3.39 (m, 4H), 3.82 (m, 4H), 4.27 (q, J=7.2 Hz, 2H), 5.38 (s, 2H), 6.80 (m, 1H), 7.10 (m, 3H), 7.29 (t, J=3.6 Hz, 1H), 7.33 (d, J=5.6 Hz, 1H), 7.36 (m, 1H), 8.03 (d, J=5.6 Hz, 1H); EIMS m/z 544 (M+1).
Sources & evidence
- ORD record
- ord-e1488b1b957247d9b18110f81a2cc147
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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