Hydrochloric Acid → HCID 19349852, compound

HRID 1636897Notes

Reaction equation

HRID 1636897 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH2:5]([C:9]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:22][CH:21]=2)[C:12]2[C:13](=[O:17])[NH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)[CH2:6][CH2:7][CH3:8].CC([O-])(C)C.[K+].Cl>CN(C=O)C>[CH2:5]([C:9]1[N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:24][CH:25]=2)[C:12]2[C:13](=[O:17])[N:14]([CH2:2][C:3]#[N:4])[CH:15]=[CH:16][C:11]=2[N:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 10385241HCID 10385241, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19349852HCID 19349852, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.79 g of chloroacetonitrile in 5 ml of DMF is added dropwise at 20°, with stirring, to a solution of 3.82 g of 2-butyl-3-(2'-cyanobiphenyl-4-ylmethyl)-4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridine and 1.17 g of potassium tert-butylate in 20 ml of DMF. The mixture is stirred at 20° for a further 30 min and poured on to ice, hydrochloric acid is added to pH 6 and the mixture is worked up in conventional manner to give 2-butyl-3-(2'-cyanobiphenyl-4-ylmethyl)-5-cyanomethyl-4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridine, m.p. 64°.

Workup

  1. additionis added to pH 6

Sources & evidence

ORD record
ord-cea7a90fb90444a1bfe83d42f60e3dd4
Source dataset
uspto-grants-2000_03
Patent number
US06037349

Reaction notes

Loading…