2-[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 → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(2-cyano-pyridin-3-yl)-phenoxy]-propyl}-thiazole-4-carboxylic acid
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31][CH2:32][CH2:33]OC3C=CC(C4C(C#N)=CSC=4)=CC=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[OH:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2[C:56]([C:61]#[N:62])=[N:57][CH:58]=[CH:59][CH:60]=2)=[CH:51][CH:50]=1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31][CH2:32][CH2:33][O:48][C:49]3[CH:54]=[CH:53][C:52]([C:55]4[C:56]([C:61]#[N:62])=[N:57][CH:58]=[CH:59][CH:60]=4)=[CH:51][CH:50]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]Participants
3
Reactant 2
Product 1
Procedure
The title compound 58 was prepared in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 58A in step 2 of Example 51: 1H NMR (DMSO-d6): δ 8.84 (dd, J=4.6, 1.53 Hz, 1H), 7.98 (dd, J=7.98, 1.53 Hz, 1H), 7.95 (d, J=7.67 Hz, 1H), 7.27-7.7 (m, 9H), 7.01-7.03 (m, 2H), 4.77 (s, 2H), 4.01 (t, J=6.29 Hz, 2H), 3.66 (t, J=5.98 Hz, 2H), 3.12-3.16 (m, 2H), 2.97 (t, J=5.98 Hz, 2H), 1.95-2.02 (m, 2H). ESI (+)/MS: 673 (M+H)+.
Sources & evidence
- ORD record
- ord-dec6f6b749384bdebc2449fbb8e40e12
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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