Serinol → HCID 71062198, compound
Reaction equation
[CH2:1]([N:5]([CH2:49][CH2:50][C:51](O)=[O:52])[C:6]([C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[N:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:36])[NH:22][S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])=[CH:17][C:16]=2[C:37]([N:39]2[CH2:48][CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40]2)=[O:38])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[NH2:54][CH:55]([CH2:58][OH:59])[CH2:56][OH:57]>>[CH2:1]([N:5]([CH2:49][CH2:50][C:51]([NH:54][CH:55]([CH2:58][OH:59])[CH2:56][OH:57])=[O:52])[C:6]([C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[N:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:36])[NH:22][S:23]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)(=[O:25])=[O:24])=[CH:17][C:16]=2[C:37]([N:39]2[CH2:48][CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40]2)=[O:38])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
Following a procedure analogous to that for the synthesis of Example 124, 3-(N-butyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxamido)propanoic acid (Intermediate 158B, 20 mg, 0.026 mmol) and 2-amino-1,3-propanediol (Aldrich, 8 mg, 0.088 mmol) were converted to the title compound (5 mg, 21%). 1H NMR (CD3OD, 1:1 mixture of amide rotamers) δ 8.72 (br s, 1H), 8.15-7.94 (m, 6.5H), 7.76-7.62 (m, 3.5H), 7.25-7.03 (m, 3.5H), 6.94-6.81 (m, 0.5H), 4.75-4.00 (m, 2H), 3.97-3.70 (m, 2H), 3.65-3.43 (m, 7H), 2.94-2.64 (m, 3H), 2.58-2.12 (m, 5H), 1.58-1.14 (m, 4H), 1.13-0.85 (m, 3H), 0.76 (t, J=7.3 Hz, 1H), 0.68 (t, J=7.5 Hz, 1H); MS(ESI+) m/z 829.4 (M+H)+.
Sources & evidence
- ORD record
- ord-319e364d3e1045abb1e97918e92cf1fc
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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