7-Benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester → 7-Benzyl-3-methyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[S:20][CH:21]=[C:22]([CH3:23])[C:8]=2[C:7]=1O)=[O:5])[CH3:2].C(OC(C1C(=O)N(CC2C=CC=CC=2)C2SC=CC=2C=1[N:47]1[CH2:52][CH2:51][N:50]([C:53]([C:55]2[S:56][CH:57]=[CH:58][CH:59]=2)=[O:54])[CH2:49][CH2:48]1)=O)C>>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[S:20][CH:21]=[C:22]([CH3:23])[C:8]=2[C:7]=1[N:47]1[CH2:52][CH2:51][N:50]([C:53]([C:55]2[S:56][CH:57]=[CH:58][CH:59]=2)=[O:54])[CH2:49][CH2:48]1)=[O:5])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
This compound was prepared from 7-benzyl-4-hydroxy-3-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyrdine-5-carboxylic acid ethyl ester (61) by applying the method described for the preparation of 7-benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (62). Yield 16%; MP 195° C. 1H-NMR (DMSO-d6) δ 1.29 (t, J=7.2 Hz, 3H), 2.53 (d, J=1.2 Hz, 3H), 4.29 (q, J=7.2 Hz, 2H), 5.27 (s, 2H), 6.94 (d, J=1.2 Hz, 1H), 7.16 (m, 1H) 7.28 (m, 3H), 7.33 (m, 2H), 7.43 (dd, J=0.8, 3.6 Hz, 1H), 7.79 (dd, J=0.8, 4.8 Hz, 1H) ppm; EIMS m/z 522 (M+1).
Sources & evidence
- ORD record
- ord-7048345e49ec4c1d977d22acca6bf75c
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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