Ammonia → 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide

HRID 1455993Notes

Reaction equation

HRID 1455993 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[CH:13][N:12]=1)[CH2:9][CH3:10].[NH3:29]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([NH2:29])=[O:19])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 113511902-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxylic acid2×

Product 1

HCID 221056502-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxylic acid (1.4 g) [table 1a, compound 2] and 1,1-carbonyldiimidazole (0.62 g) were heated in DMF at 55° C. for 3 hours. The mixture was cooled to ambient temperature, aqueous ammonia (20 ml) was added and the mixture was stirred for 18 hours. The solvent was evaporated and the residue purified by MPLC eluting with methanol: dichloromethane (5:95) to give 2-[N-(5-bromo-2-benzyloxybenzyl)-N-ethylamino]pyridine-5-carboxamide (671 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by MPLC
  3. washeluting with methanol: dichloromethane (5:95)

Sources & evidence

ORD record
ord-b4a2b0d5a6d4444eac16789f07ce05b5
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

Loading…