Trifluoroacetic acid → HCID 71273895, compound

HRID 1752459Notes

Reaction equation

HRID 1752459 reaction equation
C(OC(=O)[NH:7][C:8]1[O:9][CH2:10][C:11]([F:35])([F:34])[C@:12]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[C:17]([NH:22][C:23]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([C:32]#[N:33])=[CH:27][N:26]=3)=[O:24])[N:16]=2)([CH3:14])[N:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][C:8]1[O:9][CH2:10][C:11]([F:34])([F:35])[C@:12]([C:15]2[N:16]=[C:17]([NH:22][C:23]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([C:32]#[N:33])=[CH:27][N:26]=3)=[O:24])[CH:18]=[CH:19][C:20]=2[F:21])([CH3:14])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71271269HCID 71271269, compound

Product 1

HCID 71273895HCID 71273895, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((R)-4-{6-[(5-cyano-3-methyl-pyridine-2-carbonyl)-amino]-3-fluoro-pyridin-2-yl}-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-carbamic acid tert-butyl ester (26 mg, 0.052 mmol) and TFA (200 μl, 2.6 mmol) in dichloromethane (1.3 ml) was stirred at it for 5 hours. The reaction mixture was evaporated and the residue diluted with aq. ammonia and ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered and evaporated. 24 mg yellowish solid. Trituration with cyclohexane afforded the title compound as a slightly yellow solid. 17 mg (80% yield).

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue diluted with aq. ammonia and ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-55078e0148f34c888ba3f9c554910a09
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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