1H-imidazole-2-carbaldehyde → HCID 178447373, compound
Reaction equation
O.O.Cl.[NH2:4][C:5]([CH3:41])([CH3:40])[CH2:6][C:7]([NH:9][C@@H:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:11]1=[O:39])=[O:8].[NH:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH:47]=O>>[NH:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH2:47][NH:4][C:5]([CH3:41])([CH3:40])[CH2:6][C:7]([NH:9][C@@H:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:11]1=[O:39])=[O:8]Participants
Procedure
The title compound was prepared from 3-amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3(R)-yl]butanamide hydrochloride dihydrate and 2-imidazolecarboxaldehyde by the procedure described in Example 1. Final purification carried was out by reverse phase HPLC on C18, eluting with methanol/0.1% aqueous trifluoroacetic acid using a linear gradient of 65% methanol to 80% methanol over ten minutes; retention time approximately 5.5 min. 1H NMR (200 MHz, CD3OD): δ1.41 (s, 3H), 1.45 (s, 3H), 2.0-2.7 (m, 6H), 4.37 (dd; 8, 12 Hz; 1H), 4.51 (s, 2H), 4.83 (d, 15 Hz, 1H), 5.23 (d, 15 Hz, 1H), 6.98 (d, 8 Hz, 2H), 7.1-7.4 (m, 7H), 7.4- 7.7 (m, 5H). FAB-MS: calculated for C33H35N9O2 589; found 590 (M+H, 83%).
Workup
- customFinal purification
- washeluting with methanol/0.1% aqueous trifluoroacetic acid using a linear gradient of 65% methanol to 80% methanol over ten minutes
Sources & evidence
- ORD record
- ord-da78fde225bd4f43a85395d1d8aad5f3
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430144
Reaction notes
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