Diisopropylethylamine → 3,3,3-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)propanamide

HRID 556331Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:12])=[C:9]([NH2:11])[N:10]=2)[CH:7]=1.C(N(CC)C(C)C)(C)C.[F:22][C:23]([F:29])([F:28])[CH2:24][C:25](Cl)=[O:26]>ClCCl>[F:22][C:23]([F:29])([F:28])[CH2:24][C:25]([NH:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]2[C:8]=1[CH3:12])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

6-fluoro-3-methylimidazo[1,2-a]pyridin-2-amine (0.033 g, 0.00020 mol) was dissolved in dichloromethane (3.0 mL) and N,N-diisopropylethylamine (0.070 mL, 0.00040 mol) was added. The reaction was cooled to 0° C. and 3,3,3-trifluoropropionyl chloride (29 uL, 0.00024 mol) was added. The mixture was warmed to room temperature and was stirred for 1 hour. Solvent removed and residue was chromatographed on silca (70% ethyl acetate/hexanes) to give 3,3,3-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)propanamide Rf 0.43, 70% ethyl acetate/hexanes; MS m/z 276 (M+H). SH-SY5Y_EC50 (μM): 10.

Workup

temperatureThe mixture was warmed to room temperature
customSolvent removed
customresidue was chromatographed on silca (70% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-e51c266c3c1c4d89a5a09c5cc1bf5a09
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058274B2

Reaction notes

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