Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(3-cyano-pyrazin-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]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].[OH:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]2[C:63]([C:68]#[N:69])=[N:64][CH:65]=[CH:66][N:67]=2)=[CH:58][CH: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:55][C:56]3[CH:57]=[CH:58][C:59]([C:62]4[C:63]([C:68]#[N:69])=[N:64][CH:65]=[CH:66][N:67]=4)=[CH:60][CH:61]=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 86 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 86A: 1H NMR (DMSO-d6): δ 8.96 (d, J=2.45 Hz, 1H), 8.76 (d, J=2.45 Hz, 1H), 8.02 (d, J=7.98 Hz, 2H), 7.90-7.93 (d, J=7.98 Hz, 2H), 7.78 (d, J=7.98 Hz, 1H), 7.67 (d J=7.67 Hz, 1H), 7.33-7.49 (m, 4H), 7.11-7.15 (m, 2H), 4.84 (s, 2H), 4.1 (t, J=6.29 Hz, 2H), 3.70-3.74 (m, 2H), 3.19-3.23 (m, 2H), 3.03 (t, J=5.83 Hz, 2H), 2.02-2.09 (m, 2H). ESI (+)/MS: 674 (M+H)+.
Sources & evidence
- ORD record
- ord-9dc124f0057b44e1b02c16e1dc99d93b
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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