2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-isopropylamino-thieno[3,2-d]pyrimidin-7-yl)-phenoxy]-propyl}-thiazole-4-carboxylic acid
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31][CH2:32][CH2:33][O:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]4[C:45](C#N)=[CH:44][S:43][CH:42]=4)=[CH:37][CH:36]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].C([NH:51][C:52]1[C:53]2SC=[C:58](C3C=CC(O)=CC=3)[C:54]=2[N:55]=[CH:56][N:57]=1)(C)C>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31][CH2:32][CH2:33][O:34][C:35]3[CH:36]=[CH:37][C:38]([C:41]4[C:45]5[N:51]=[CH:52][N:57]=[C:56]([NH:55][CH:54]([CH3:58])[CH3:53])[C:44]=5[S:43][CH:42]=4)=[CH:39][CH:40]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]Participants
3
Reactant 2
Product 1
Procedure
The title compound 69 was prepared in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 69B: 1H NMR (DMSO-d6): δ 8.59 (s, 1H), 8.25 (s, 1H), 8.00 (d, J=7.67 Hz, 1H), 7.66-7.79 (m, 4H), 7.32-7.48 (m, 4H), 7.03 (d, J=8.59 Hz, 2H), 4.84 (s, 2H), 4.41-4.47 (m, 1H), 4.05 (t, J=6.14 Hz, 2H), 3.72-3.75 (m, 2H), 3.19-3.22 (m, 2H), 3.03 (t, J=5.98 Hz, 2H), 2.00-2.08 (m, 2H), 1.28 (d, J=6.44 Hz, 6H). ESI (+)/MS: 762 (M+H)+.
Sources & evidence
- ORD record
- ord-796d9f8d78684bdfb69d34112b24e4f4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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