Hydrochloric Acid → (S)-4-Cyano-N-(2-fluoro-4-(morpholin-2-yl)phenyl)picolinamide hydrochloride

HRID 571847Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][N:24]=3)=[O:22])=[C:16]([F:31])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.[ClH:32].O1CCOCC1>C1COCC1>[ClH:32].[C:29]([C:27]1[CH:26]=[CH:25][N:24]=[C:23]([C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([C@@H:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:15][C:16]=2[F:31])=[O:22])[CH:28]=1)#[N:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-2-{4-[(4-Cyano-pyridine-2-carbonyl)-amino]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (73 mg, 171 μmol, Eq: 1.00) in THF (3 ml) was added 4M−HCl in dioxane (0.642 ml, 2.52 mmol, Eq: 15). The reaction mixture was stirred at 60° C. for 5 h. To the cooled mixture was then added ethyl acetate and the suspension was filtered off and dried under high vacuo to give the target compound as a white solid (53 mg, 85%). MS (ISP): 325.2 ([M+H]+).

Workup

filtrationadded ethyl acetate and the suspension was filtered off
customdried under high vacuo

Sources & evidence

ORD record: ord-6e1e2bafeab441b28986fd38cb87ee6c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029370B2

Reaction notes

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