Pyridine → 8-[2-(4-Chlorobutyrylamino)-6-methylbenzylamino]-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1955002Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1.C(=O)([O-])O.[K+]>ClCCl.O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:8][C:9]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH3:23])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:6]

Participants

Conditions

Temperature: 10 °C

Procedure

0.88 ml (7.85 mmol) of 4-chlorobutyryl chloride is added dropwise at 0-5° C. with stirring to a solution of 2.2 g (7.85 mmol) of 8-(2-amino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine and 0.63 ml (7.85 mmol) of pyridine in 30 ml of dichloromethane and the mixture is stirred for a further 2 h at 0-20° C. It is treated with water and potassium hydrogen carbonate to pH 7, the mixture is extracted with shaking, and the organic layer is dried with magnesium sulfate and concentrated in vacuo. The residue is recrystallized from toluene and petroleum ether (50/70° C.). 2.6 g (86%) of the title compound are obtained. M.p. 138-140° C.

Workup

extractionthe mixture is extracted
stirringwith shaking
dry with materialthe organic layer is dried with magnesium sulfate
concentrationconcentrated in vacuo
customThe residue is recrystallized from toluene and petroleum ether (50/70° C.)

Sources & evidence

ORD record: ord-a7a7bf1430f74ce68ea4d7fb3651938b
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124313

Reaction notes

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