Water → HCID 22485109, compound

HRID 1368256Notes

Reaction equation

HRID 1368256 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.ON1C2C=CC=CC=2N=N1.[Br:34][CH2:35][CH2:36][CH2:37][C:38](O)=[O:39].O>CN(C)C=O.Cl.CN(C)CCCN=C=NCC>[Br:34][CH2:35][CH2:36][CH2:37][C:38]([NH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1)=[O:39]

Participants

7

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 758094-Bromobutyric acidHCID 22388007HCID 22388007, compound

Product 1

HCID 22485109HCID 22485109, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (450 mg) was suspended in N,N-dimethylformamide (5 ml) and 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (391 mg), 1-hydroxybenzotriazole (276 mg) and 4-bromobutanoic acid (318 mg) were added, which was followed by stirring at room temperature for 24 hr. Water (50 ml) was added to the reaction mixture under ice-cooling and the precipitated crystals were collected by filtration and dried under reduced pressure with heating to give methyl 3-(4-((4-bromobutyryl)amino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (436 mg) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. customdried under reduced pressure
  4. temperaturewith heating

Sources & evidence

ORD record
ord-c05df82036794e29b45b2de30f8423c4
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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