Trifluoroacetic acid → HCID 59447525, compound

HRID 1518363Notes

Reaction equation

HRID 1518363 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]4[C:52](C#N)=[CH:51][S:50][CH:49]=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([CH2:60][CH2:61][CH2:62][NH:63][C:64]2C3SC=C(C4C=CC(O)=CC=4)C=3[N:67]=[CH:68][N:69]=2)[CH2:59][CH2:58][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:43]=[CH:44][C:45]([C:48]4[C:52]5[N:67]=[CH:68][N:69]=[C:64]([NH:63][CH2:62][CH2:61][CH2:60][N:55]6[CH2:56][CH2:57][CH2:58][CH2:59]6)[C:51]=5[S:50][CH:49]=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

HCID 6422Trifluoroacetic acidHCID 468362452-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acidHCID 59447654HCID 59447654, compound

Product 1

HCID 59447525HCID 59447525, compound

Procedure

The title compound 78 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 78B: 1H NMR (DMSO-d6): δ 12.82 (s, 1H), 9.53 (s, 1H), 8.52 (s, 1H), 8.22 (s, 1H), 8.03-8.07 (m, 1H), 8.01 (d, J=7.98 Hz, 1H), 7.69 (d, J=8.59 Hz, 1H), 7.79 (d, J=7.98 Hz, 1H), 7.67 (d, J=7.36 Hz, 1H), 7.32-7.49 (m, 4H), 7.01 (d, J=8.9 Hz, 2H), 4.84 (s, 2H), 4.04 (t, J=6.29 Hz, 2H), 3.73 (t, J=5.83 Hz, 2H), 3.18-3.24 (m, 4H), 3.01-3.05 (m, 4H), 1.78-2.07 (m, 6H). ESI (+)/MS: 831 (M+H)+.

Sources & evidence

ORD record
ord-fcf8bc5f472a494bb2f8b14d09a38168
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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