Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(3-{4-[5-(2-dimethylamino-ethoxy)-pyridin-2-yl]-phenoxy}-propyl)-thiazole-4-carboxylic acid
Reaction equation
C(O)(C(F)(F)F)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[CH2:28][N:27]([C:30]1[S:31][C:32]([CH2:38][CH2:39][CH2:40][O:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]4C(C#N)=CS[CH:49]=4)=[CH:44][CH:43]=3)=[C:33]([C:35]([OH:37])=[O:36])[N:34]=1)[CH2:26][CH2:25]2)=[O:19].[CH3:55][N:56]([CH3:73])[CH2:57][CH2:58][O:59][C:60]1[CH:61]=CC(C2C=CC(O)=CC=2)=[N:64][CH:65]=1>>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[CH2:28][N:27]([C:30]1[S:31][C:32]([CH2:38][CH2:39][CH2:40][O:41][C:42]3[CH:43]=[CH:44][C:45]([C:46]4[CH:47]=[CH:61][C:60]([O:59][CH2:58][CH2:57][N:56]([CH3:73])[CH3:55])=[CH:65][N:64]=4)=[CH:48][CH:49]=3)=[C:33]([C:35]([OH:37])=[O:36])[N:34]=1)[CH2:26][CH2:25]2)=[O:19]Participants
4
Reactant 3
Product 1
Procedure
The title compound 90 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 90B: 1H NMR (DMSO-d6): δ 9.60 (s, 1H), 8.09 (d, J=2.76 Hz, 1H), 8.02 (d, J=7.37 Hz, 1H), 7.93 (d, J=8.9 Hz, 2H), 7.85 (d, J=8.9 Hz, 1H), 7.79 (d, J=8.29 Hz, 1H), 7.67 (d, J=7.67 Hz, 1H), 7.33-7.51 (m, 5H), 6.99 (d, J=8.9 Hz, 2H), 4.84 (s, 2H), 4.42-4.45 (m, 2H), 4.04 (d, J=6.29 Hz, 2H), 3.83 (d, J=5.83 Hz, 1H), 3.55 (br, 2H), 3.16-3.21 (m, 2H), 3.03 (t, J=5.83 Hz, 2H), 2.89 (s, 6H), 1.99-2.07 (m, 2H). ESI (+)/MS: 735 (M+H)+.
Sources & evidence
- ORD record
- ord-a12a1b90b2a74338ae73c0ea8fd0bdd6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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