Trifluoroacetic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-methyl-piperazin-1-yl)-phenoxy]-propyl}-thiazole-4-carboxylic acid

HRID 1518369

Reaktionsgleichung

Reaktionsgleichung von HRID 1518369
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](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:47]=[CH:46][C:45]([N:59]4[CH2:60][CH2:61][N:56]([CH3:55])[CH2:57][CH2:58]4)=[CH:44][CH:43]=3)=[C:33]([C:35]([OH:37])=[O:36])[N:34]=1)[CH2:26][CH2:25]2)=[O:19]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 116224864-(4-Methyl-1-piperazinyl)phenolHCID 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 acid

Produkt 1

HCID 594476302-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-methyl-piperazin-1-yl)-phenoxy]-propyl}-thiazole-4-carboxylic acid

Versuchsvorschrift

The title compound 82 was prepared as a TFA salt in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 82A: 1H NMR (DMSO-d6): δ 12.90 (s, 1H), 9.58 (s, 1H), 8.04 (d, J=7.63 Hz, 2H), 7.80 (d, J=7.93 Hz, 2H), 7.67 (d, J=7.63 Hz, 1H), 7.35-7.50 (m, 4H), 6.90-6.92 (m, 2H), 6.82-6.85 (m, 2H), 4.83 (s, 2H), 3.91 (t, J=6.26 Hz, 2H), 3.14-3.17 (m, 2H), 3.03 (t, J=5.95 Hz, 2.82-2.86 (m, 5H), 1.94-2.00 (m, 2H). ESI (+)/MS: 669 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-1c2e49d06b034d27865968c212f2ad4e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232273B2

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