Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[3-(4-methyl-piperazin-1-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]OC3C=CC(C4C(C#N)=CSC=4)=CC=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]([C:62]2[CH:63]=[C:64]([OH:68])[CH:65]=[CH:66][CH:67]=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:68][C:64]3[CH:65]=[CH:66][CH:67]=[C:62]([N:59]4[CH2:58][CH2:57][N:56]([CH3:55])[CH2:61][CH2:60]4)[CH:63]=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 87 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 87A: 1H NMR (DMSO-d6): δ 12.85 (s, 1H), 9.65 (s, 1H), 8.03 (d, J=7.67 Hz, 1H), 7.79 (d, J=7.98 Hz, 2H), 7.67 (d, J=7.67 Hz, 1H), 7.34-7.50 (m, 4H), 7.12 (t, J=8.13 Hz, 1H), 6.54 (dd, J=8.13, 2.3 Hz, 1H), 6.50 (t, J=2.15 Hz, 1H), 6.42 (dd, J=8.29, 2.15 Hz, 1H), 4.83 (s, 2H), 3.96 (t, J=6.29 Hz, 2H), 3.73 (t, J=5.83 Hz, 2H), 3.10-3.18 (m, 5H), 3.03 (t, J=5.98 Hz, 2H), 2.90-2.98 (m, 2H), 2.85 (s, 3H), 1.95-2.02 (m, 2H). ESI (+)/MS: 669 M+H)+.
Sources & evidence
- ORD record
- ord-129e699bdd154d2381caa0c3431430a4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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