Trifluoroacetic acid → [2-Amino-6-(piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone

HRID 30107Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])=[C:17]([NH2:30])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:30][C:17]1[C:18]([C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])=[O:29])=[CH:19][CH:20]=[C:15]([NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-[6-Amino-5-(2-fluoro-benzoyl)-pyridin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (269.6 mg, 0.6504 mmol, Example 8) was dissolved in dichloromethane (5 mL), cooled to 0° C. and treated with trifluoroacetic acid (2.5 mL). After stirring ˜30 minutes, the reaction mixture was concentrated in vacuo. The salt was then neutralized with saturated sodium carbonate (˜3 mL), extracted with ethyl acetate/methylene chloride (˜50 mL), washed with saturated sodium chloride (˜3 mL), dried over sodium sulfate and evaporated in vacuo to give [2-Amino-6-(piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone as an off-white solid (200 mg, 0.636 mmol, 98 % yield).

Workup

concentrationthe reaction mixture was concentrated in vacuo
extractionextracted with ethyl acetate/methylene chloride (˜50 mL)
washwashed with saturated sodium chloride (˜3 mL)
dry with materialdried over sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-a348506a84874df8b2123a5803a5eaae
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423051B2

Reaction notes

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