Trifluoroacetic acid → HCID 52913937, compound

HRID 540763Notes

Reaction equation

HRID 540763 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[N:13]([CH2:14][CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([C:22]([NH2:25])([CH3:24])[CH3:23])[CH:19]=[CH:20][CH:21]=3)[CH:10]=2)=[CH:6][CH:5]=1.[F:30][C:31]([F:38])([F:37])[CH2:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[CH2:14]([N:13]1[C:9]([O:8][C:7]2[CH:26]=[CH:27][C:4]([CH:3]=[O:2])=[CH:5][CH:6]=2)=[CH:10][C:11]([C:16]2[CH:17]=[C:18]([C:22]([NH:25][S:33]([CH2:32][C:31]([F:38])([F:37])[F:30])(=[O:35])=[O:34])([CH3:24])[CH3:23])[CH:19]=[CH:20][CH:21]=2)=[N:12]1)[CH3:15]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 67111600HCID 67111600, compound

Product 1

HCID 52913937HCID 52913937, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(3-{5-[4-(dimethoxymethyl)phenoxy]-1-ethyl-1H-pyrazol-3-yl}phenyl)propan-2-amine (8.84 g, 22.35 mmol, 1 equiv) was stirred at −78° C. in anhydrous DCM (224 mL). 2,2,2-trifluoroethanesulfonyl chloride (4.90 g, 26.80 mmol, 1.2 equiv) was added, followed by triethylamine (4.67 mL, 33.50 mmol, 1.5 equiv). After stirring at −78° C. for 10 minutes the cooling bath was removed and the mixture was allowed to slowly warm to 22° C. Upon reaching 22° C. 7:1 Water:TFA (4.5 equiv) was added to the vigorously stirring reaction mixture. After stirring for 1 hour the mixture was partitioned between water and DCM. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the N-(2-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}propan-2-yl)-2,2,2-trifluoroethanesulfonamide (98% Yield). Calcd (M+1)+: 496.1. Found: 496.1.

Workup

  1. customwas removed
  2. temperatureto slowly warm to 22° C
  3. customUpon reaching 22° C
  4. stirringvigorously stirring
  5. customreaction mixture
  6. stirringAfter stirring for 1 hour the mixture
  7. customwas partitioned between water and DCM
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23f00ed4ec214e1482648ecebf78dd72
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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