4-Pyridinecarboxaldehyde → HCID 10600813, compound

HRID 2121263Notes

Reaction equation

HRID 2121263 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[N:30]1[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][CH:31]=1>CO>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:25][CH:26]([CH3:27])[CH3:28])[NH:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:36][C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)=[CH:9][C:8]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 20622740HCID 20622740, compound

Product 1

HCID 10600813HCID 10600813, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was synthesized via the reductive amination of N-[4-amino-2-naphth-1-ylbenzoyl]leucine methyl ester and pyridine-4-carboxaldehyde in methanol to afford, after purification, a white solid. 1H NMR (DMSO-d6) δ 0.71 (d, J=5.45 Hz, 3H), 0.82 (d, J=5.13 Hz, 3H), 1.20-1.27 (m, 2H), 1.29-1.32 (m, 1H), 3.72 (s, 2H), 3.79 (s, 1H), 4.15 (m, 1H), 4.41 (d, 2H, CH2), 5.52 (d, 1H, NH), 6.67-6.75 (dd, 1H), 6.89 (d, 1H), 7.23 (m, 2H), 7.25-7.35 (m, 8H), 8.55 (m, 2H).

Workup

  1. customto afford
  2. customafter purification

Sources & evidence

ORD record
ord-20a48f1a81db4c0b841e79d62be551e0
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…