Dichloromethane → N-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-benzyl]-2-(m-trifluoromethyl-phenyl)-acetamide

HRID 1446761Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.C(Cl)Cl.[F:22][C:23]([F:35])([F:34])[C:24]1[CH:25]=[C:26]([CH2:30][C:31](Cl)=[O:32])[CH:27]=[CH:28][CH:29]=1.C(NCC)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:31](=[O:32])[CH2:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:34])([F:22])[F:35])[CH:25]=4)=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In a 40 mL septum capped vial purged with N2, add 4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-benzylamine (125 mg, 0.48 mmol), magnetic stir bar, CH2Cl2 (6 mL), cool the vial in an ice bath and slowly add 1 mL (CH2Cl2 solution of m-trifluoromethyl-phenylacetyl chloride, 0.48 mmol). Add isopropyl ethyl amine (0.8 mL) with THF (2 mL). Remove the vial from the ice bath and heat to 40° C. for 6 hours. Add a trace of MeOH and evaporate the solvents under vacuum and take up the oil into a minimal amount of CH2Cl2 and chromatograph using SiO2 eluting with a gradient of 0.5% to 5% of 2 M NH3 in MeOH with the balance CH2Cl2. Isolate the product, dry in a vacuum oven at 40° C. for 24 hours to give 144 mg (67%) MS (ES), m/z 444 (M+1).

Workup

custompurged with N2
temperaturecool the vial in an ice bath
customRemove the vial from the ice bath
additionAdd a trace of MeOH
customevaporate the solvents under vacuum
customIsolate the product
customdry in a vacuum oven at 40° C. for 24 hours
customto give 144 mg (67%)

Sources & evidence

ORD record: ord-df8d8fe985d9415cb70b2381b4c8a407
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666879B2

Reaction notes

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