1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone → 5-{3-[4-(4-Acetyl-piperazin-1-yl)-phenoxy]-propyl}-2-[8-(benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-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][O:34][C:35]3[CH:40]=[CH:39][C:38](C4C(C#N)=CSC=4)=[CH:37][CH:36]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].OC1C=CC([N:55]2[CH2:60][CH2:59][N:58]([C:61](=[O:63])[CH3:62])[CH2:57][CH2:56]2)=CC=1>>[C:61]([N:58]1[CH2:59][CH2:60][N:55]([C:38]2[CH:37]=[CH:36][C:35]([O:34][CH2:33][CH2:32][CH2:31][C:25]3[S:24][C:23]([N:20]4[CH2:19][CH2:18][C:17]5[C:22](=[C:13]([C:11](=[O:12])[NH:10][C:2]6[S:1][C:5]7[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=7[N:3]=6)[CH:14]=[CH:15][CH:16]=5)[CH2:21]4)=[N:27][C:26]=3[C:28]([OH:30])=[O:29])=[CH:40][CH:39]=2)[CH2:56][CH2:57]1)(=[O:63])[CH3:62]Participants
3
Reactant 2
Product 1
Procedure
The title compound 61 was prepared in a similar manner to the synthesis of compound 51 by substituting compound 51A with 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in step 2 of Example 51: 1H NMR (DMSO-d6): δ 8.02 (d, J=7.36 Hz, 1H), 7.78 (d, J=8.29 Hz, 1H), 7.66 (d, J=7.06 Hz, 1H), 7.33-7.49 (m, 4H), 6.90-6.92 (m, 2H), 6.80-6.82 (m, 2H), 4.82 (s, 2H), 3.90 (t, J=6.29 Hz, 2H), 3.71 (t, J=6.29 Hz, 2H), 3.53-3.56 (m, 2H), 3.13-3.17 (m, 2H), 3.02 (t, J=5.37 Hz, 4H), 2.94-2.96 (m, 2H), 2.02 (s, 3H), 1.92-1.99 (m, 2H). ESI (+)/MS: 697 (M+H)+.
Sources & evidence
- ORD record
- ord-cc777dcf91984311ba9516010dc49bea
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232273B2
Reaction notes
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