Trifluoroacetic acid → HCID 71112733, compound

HRID 571824Notes

Reaction equation

HRID 571824 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][O:18][C@H:17]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[N:31]([CH3:41])[N:32]=[C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:34]=3)=[O:29])=[C:23]([F:42])[CH:22]=2)[CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>O.C(#N)C>[F:42][C:23]1[CH:22]=[C:21]([C@H:17]2[O:18][CH2:19][CH2:20][NH:15][CH2:16]2)[CH:26]=[CH:25][C:24]=1[NH:27][C:28]([C:30]1[N:31]([CH3:41])[N:32]=[C:33]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:34]=1)=[O:29]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 71086979HCID 71086979, compound

Product 1

HCID 71112733HCID 71112733, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (124 μl) in water (4 ml) was added a solution of (R)-2-{3-fluoro-4-[(2-methyl-5-phenyl-2H-pyrazole-3-carbonyl)-amino]-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (78 mg) in acetonitrile (2 ml). The reaction mixture was then capped and the mixture was shaken at 80° C. for 4 h. The reaction mixture was then cooled to room temperature and poured into 1 M aq. NaOH and the resulting mixture was extracted twice with EtOAc. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis); gradient: EtOAc/heptane) to afford 2-methyl-5-phenyl-2H-pyrazole-3-carboxylic acid ((R)-2-fluoro-4-morpholin-2-yl-phenyl)-amide (49 mg, 79%) as a white solid. MS (ISP): 381.3 ([M+H]+).

Workup

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. extractionthe resulting mixture was extracted twice with EtOAc
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis)

Sources & evidence

ORD record
ord-a349b4cd84124cab946b93c4ba14feb7
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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