2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-[5-(4-cyano-thiophen-3-yl)-2-hydroxy-benzyl]-thiazole-4-carboxylic acid
Reaction equation
S1C2C=CC=CC=2N=C1NC(C1C=CC=C2C=1CN(C1SC(C3C=CC(CO)=CC=3)=C(C(O)=O)N=1)CC2)=O.[C:39]([C:41]1[C:42]([C:46]2[CH:47]=[CH:48][C:49]([OH:92])=[C:50]([CH:91]=2)[CH2:51][C:52]2[S:56][C:55]([N:57]3[CH2:66][CH2:65][C:64]4[C:59](=[C:60]([C:67](=[O:86])/[N:68]=[C:69]5/[S:70][C:71]6[CH:85]=[CH:84][CH:83]=[CH:82][C:72]=6[N:73]/5COCC[Si](C)(C)C)[CH:61]=[CH:62][CH:63]=4)[CH2:58]3)=[N:54][C:53]=2[C:87]([O:89]C)=[O:88])=[CH:43][S:44][CH:45]=1)#[N:40]>>[S:70]1[C:71]2[CH:85]=[CH:84][CH:83]=[CH:82][C:72]=2[N:73]=[C:69]1[NH:68][C:67]([C:60]1[CH:61]=[CH:62][CH:63]=[C:64]2[C:59]=1[CH2:58][N:57]([C:55]1[S:56][C:52]([CH2:51][C:50]3[CH:91]=[C:46]([C:42]4[C:41]([C:39]#[N:40])=[CH:45][S:44][CH:43]=4)[CH:47]=[CH:48][C:49]=3[OH:92])=[C:53]([C:87]([OH:89])=[O:88])[N:54]=1)[CH2:66][CH2:65]2)=[O:86]Participants
3
Reactant 2
Product 1
Procedure
The title compound 60 was prepared in a similar manner to the synthesis of compound 34 by substituting compound 34D with compound 60A: 1H NMR (DMSO-d6): δ 9.92 (s, 1H), 8.55 (d, J=3.07 Hz, 1H), 8.00 (d, J=7.98 Hz, 1H), 7.77 (d, J=8.29 Hz, 1H), 7.63-7.66 (m, 2H), 7.29-7.48 (m, 6H), 6.90 (d, J=8.29 Hz, 1H), 4.79 (s, 2H), 4.34 (s, 2H), 3.66 (d, J=5.98 Hz, 2H), 2.99 (t, J=5.83 Hz, 2H). ESI (+)/MS: 650 (M+H)+.
Sources & evidence
- ORD record
- ord-13438dd278ef4be6abc1bed4812f50d1
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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