Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-[3-(4-pyrimidin-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)=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].[N:55]1[CH:60]=[CH:59][CH:58]=[N:57]C=1C1C=CC(O)=CC=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:48]4[N:57]=[CH:58][CH:59]=[CH:60][N:55]=4)=[CH:46][CH:47]=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 81 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 81A: 1H NMR (DMSO-d6): δ 8.83 (d, J=4.88 Hz, 2H), 8.32 (d, J=8.85 Hz, 2H), 8.03 (d, J=4.88 Hz, 1H), 7.79 (d, J=8.85 Hz, 1H), 7.67 (d, J=7.63 Hz, 1H), 7.34-7.49 (m, 5H), 7.04 (d, J=8.85 Hz, 2H), 4.84 (s, 2H), 4.07 (t, J=6.26 Hz, 2H), 3.72 (t, J=5.95 Hz, 2H), 3.18-3.12 (m, 2H), 3.03 (t, J=5.64 Hz, 2H), 2.01-2.07 (m, 2H). ESI (+)/MS: 649 (M+H)+.
Sources & evidence
- ORD record
- ord-b056753741ea4e1d98bf9611c565ff5b
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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