1H-imidazole-2-carbaldehyde → HCID 69892500, compound

HRID 2121257Notes

Reaction equation

HRID 2121257 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH:32]=O.CC(C[C@H](NC(C1C=CC(NCC2NC=NC=2)=CC=1C1C=CC=CC=1)=O)C(O)=O)C>>[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:32][C:28]2[NH:27][CH:31]=[CH:30][N:29]=2)=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 10645020HCID 10645020, compoundHCID 20622897HCID 20622897, compound

Product 1

HCID 69892500HCID 69892500, compound

Procedure

Reductive animation of N-[4-amino-2-phenylbenzoyl]-L-leucine methylester hydrochloride and imidazole-2-carboxaldehyde following similar procedures to those described for GGTI-2132 afforded after purification N-[4-(Imidazol-2-ylmethylamino)-2-phenylbenzoyl]leucine methyl ester as a white solid. 42%. mp=156-160° C. 1H NMR (DMSO-d6) 8.19 (m, 1H, aryl), 7.58 (s, 2H), 7.34-7.22 (m, 6H), 6.67 (d, 1H, J=8.3 Hz), 6.60 (s, 1H), 4.72 (s, 2H, CH2), 4.17 (m, 1H), 3.59 (s, 3H), 1.52-1.35 (m, 3H), 0.80 (d, 3H, J=5.3 Hz), 0.75 (d, 3H, J=5.04 Hz).

Workup

  1. customafforded
  2. customafter purification N-[4-(Imidazol-2-ylmethylamino)-2-phenylbenzoyl]leucine methyl ester as a white solid

Sources & evidence

ORD record
ord-c77f1c89b11f48dc82a19aa2e6a58106
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…