Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-methyl-piperazin-1-ylmethyl)-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].[CH3:55][N:56]1[CH2:61][CH2:60][N:59]([CH2:62]C2C=CC(O)=CC=2)[CH2:58][CH2:57]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]([CH2:55][N:56]4[CH2:61][CH2:60][N:59]([CH3:62])[CH2:58][CH2:57]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 89 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 89A: 1H NMR (DMSO-d6): δ 8.03 (d, J=7.67 Hz, 1H), 7.79 (d, J=7.98 Hz, 1H), 7.67 (d, J=7.06 Hz, 1H), 7.34-7.50 (m, 4H), 7.28 (d, J=8.59 Hz, 2H), 6.93 (d, J=8.59 Hz, 2H), 4.83 (s, 2H), 3.98 (d, J=6.29 Hz, 2H), 3.16-3.19 (m, 4H), 3.03 (t, J=5.83 Hz, 2H), 2.76 (s, 3H), 1.97-2.03 (m, 2H). ESI (+)/MS: 683 (M+H)+.
Sources & evidence
- ORD record
- ord-d024d98edd7b488c8e9120e77f4e4a78
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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