Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(2-morpholin-4-yl-ethoxy)-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](C4C(C#N)=CSC=4)=[CH:44][CH:43]=3)=[C:33]([C:35]([OH:37])=[O:36])[N:34]=1)[CH2:26][CH2:25]2)=[O:19].[O:55]1[CH2:60][CH2:59][N:58]([CH2:61][CH2:62][O:63]C2C=CC(O)=CC=2)[CH2:57][CH2:56]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:47]=[CH:46][C:45]([O:63][CH2:62][CH2:61][N:58]4[CH2:59][CH2:60][O:55][CH2:56][CH2:57]4)=[CH:44][CH:43]=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 88 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 88B: 1H NMR (DMSO-d6): δ 12.86 (s, 1H), 9.96 (s, 1H), 8.03 (d, J=7.98 Hz, 1H), 7.79 (d, J=7.98 Hz, 2H), 7.67 (d, J=7.36 Hz, 1H), 6.86-6.94 (m, 4H), 4.83 (s, 2H), 4.25-4.27 (m, 2H), 3.91-4.02 (m, 4H), 3.73 (t, J=5.98 Hz, 2H), 3.14-3.22 (m, 4H), 3.03 (t, J=5.98 Hz, 2H), 1.94-2.01 (m, 2H). ESI (+)/MS: 700 (M+H)+.
Sources & evidence
- ORD record
- ord-6143e036a1514b4a971e5a70387ef90d
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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