Trifluoroacetic acid → HCID 71086881, compound

HRID 571827Notes

Reaction equation

HRID 571827 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[C:12]([CH:31]2[O:36][CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]2)[CH:13]=[CH:14][C:15]=1[NH:16][C:17]([C:19]1[CH:23]=[CH:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:20]=1)=[O:18])#[N:9].[OH-].[Na+]>O.C(#N)C>[C:8]([C:10]1[CH:11]=[C:12]([CH:31]2[O:36][CH2:35][CH2:34][NH:33][CH2:32]2)[CH:13]=[CH:14][C:15]=1[NH:16][C:17]([C:19]1[CH:23]=[CH:22][N:21]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[N:20]=1)=[O:18])#[N:9]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86674687HCID 86674687, compound

Product 1

HCID 71086881HCID 71086881, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (84 μl) in water (4.5 ml) was added a solution of tert-butyl (RS)-2-(3-cyano-4-(1-(4-fluorophenyl)-1H-pyrazole-3-carboxamido)phenyl)morpholine-4-carboxylate (41 mg) in acetonitrile (2 ml). The reaction mixture was then capped and the mixture was shaken at 80° C. for 5 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 (SiO2; gradient: 0% to 10% methanol in dichloromethane) to afford (RS)—N-(2-cyano-4-(morpholin-2-yl)phenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamide (20 mg, 61%) as a white solid. MS (ISP): 392.2 ([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 (SiO2; gradient: 0% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8ed397aff6b84fd58fb1be7a72e7b82a
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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