Methanol → 3-Cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-ylamine

HRID 556313Notes

Reaction equation

[OH-].[Na+].[CH:3]1([C:6]2[N:10]3[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]3=[N:8][C:7]=2[NH:16]C(=O)C(F)(F)F)[CH2:5][CH2:4]1.CO.O1CCCC1>O>[CH:3]1([C:6]2[N:10]3[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]3=[N:8][C:7]=2[NH2:16])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 55 °C

Procedure

6.00 M of Sodium hydroxide in water (1.0 mL) was added to a solution of N-(3-Cyclopropyl-6-fluoro-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoro-acetamide (compound e, 0.197 g, 0.000617 mol) in Methanol (2.00 mL, 0.0494 mol) and Tetrahydrofuran (2.0 mL, 0.0246 mol) and the reaction mixture was stirred at 55° C. for 36 hours. The reaction mixture concentrated in vacuo to dryness and crude product purified by column chromatography (5% methanol/dichloromethane) as a yellow solid. Rf 0.41, 5% methanol/dichloromethane; MS m/z 192 (M+H).

Workup

concentrationThe reaction mixture concentrated in vacuo to dryness and crude product
custompurified by column chromatography (5% methanol/dichloromethane) as a yellow solid

Sources & evidence

ORD record: ord-54f69bdf2bd846a7993e674eb8696ce2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058274B2

Reaction notes

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