Trifluoroacetic acid → rac-N-(1-(pyrrolidin-2-ylmethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

HRID 624080Notes

Reaction equation

HRID 624080 reaction equation
[C:1]1([CH3:33])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([NH:14][C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][N:22]3C(OC(C)(C)C)=O)[CH:19]=2)=[O:13])[CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:22]1[CH2:23][CH2:24][CH2:25][CH:21]1[CH2:20][N:18]1[CH:19]=[C:15]([NH:14][C:12]([C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:3]2[CH:2]=[C:1]([CH3:33])[CH:6]=[CH:5][CH:4]=2)=[O:13])[CH:16]=[N:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735188rac-tert-butyl 2-((4-(5-(m-tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 123442042rac-N-(1-(pyrrolidin-2-ylmethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-tert-butyl 2-((4-(5-(m-tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)methyl)pyrrolidine-1-carboxylate (100 mg, 0.22 mmol) in DCM (2.3 mL), TFA (0.170 mL, 2.215 mmol) was added at 0° C. After stirring for 5 h at rt, the solvent and the remaining TFA was removed under reduced pressure. The residue was dissolved in DCM and 1 N aq. NaOH-solution was added until basic. The layers were separated and the aq. layer was extracted with DCM (1×). The combined organic layers were washed with brine, dired (MgSO4), filterd and the solvent was removed under reduced pressure to yield rac-N-(1-(pyrrolidin-2-ylmethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide a yellow oil which was used in the next step without further purification. LC-MS conditions A: tR=0.62 min, [M+H]+=352.07.

Workup

  1. customthe solvent and the remaining TFA was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM
  3. addition1 N aq. NaOH-solution was added until basic
  4. customThe layers were separated
  5. extractionthe aq. layer was extracted with DCM (1×)
  6. washThe combined organic layers were washed with brine, dired (MgSO4), filterd
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e15c84ff30e64aeab32eb2266593a3db
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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