Trifluoroacetic acid → HCID 67110819, compound

HRID 540800Notes

Reaction equation

HRID 540800 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([O:7][C:8]2[N:12]([CH2:13][C:14]3[N:15]=[CH:16][O:17][CH:18]=3)[N:11]=[C:10]([C:19]3[CH:20]=[C:21]([C:25]4([NH:29]C(=O)OC(C)(C)C)[CH2:28][O:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)[CH:9]=2)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]1[CH:18]=[C:14]([CH2:13][N:12]2[C:8]([O:7][C:6]3[CH:37]=[CH:38][C:3]([C:2]([F:1])([F:39])[F:40])=[CH:4][CH:5]=3)=[CH:9][C:10]([C:19]3[CH:20]=[C:21]([C:25]4([NH2:29])[CH2:28][O:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)=[N:11]2)[N:15]=[CH:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69933203HCID 69933203, compound

Product 1

HCID 67110819HCID 67110819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl (3-{3-[5-(4-trifluoromethylphenoxy)-1-(1,3-oxazol-4-ylmethyl)-1H-pyrazol-3-yl]phenyl}oxetan-3-yl)carbamate (48 mg, 0.086 mmol) in 0.6 mL of CH2Cl2 was cooled in an ice bath, and to the solution was added 0.6 mL of TFA. The solution was stirred for 1.5 h and then quenched with 10% Na2CO3. The organic phase was washed with water and brine, dried over Na2SO4, and the solvent was removed under reduced pressure to give 3-{3-[1-(1,3-oxazol-4-ylmethyl)-5-(4-trifluoromethylphenoxy)-1H-pyrazol-3-yl]phenyl}oxetan-3-amine as a glass. Calcd (M+1)+: 457.4. found: 457.1.

Workup

  1. customquenched with 10% Na2CO3
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d52cc8e67a2949c1825dabe38c328d02
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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