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

HRID 624073Notes

Reaction equation

HRID 624073 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([NH:15][C:16]([C:18]2[N:19]=[CH:20][O:21][C:22]=2[C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[O:17])[CH:12]=[N:11]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([NH:15][C:16]([C:18]2[N:19]=[CH:20][O:21][C:22]=2[C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[O:17])[CH:12]=[N:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86704223HCID 86704223, compound

Product 1

HCID 86704224N-(1-(2-Aminoethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl(2-(4-(5-(m-tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)ethyl)carbamate (4.29 g, 10.426 mmol) in DCM (60 mL), TFA (12 mL, 156.39 mmol) was added at 0° C. After strring for 1 h at rt, the reaction mixture was concentrated. The residue was dissolved in DCM and 2 N aq. NaOH-solution was added. The org. layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and the solvent removed to yield the title compound as a white solid, which was used in the next step without further purification. LC-MS conditions B: tR=0.54 min, [M+H]+=312.31.

Workup

  1. additionwas added at 0° C
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in DCM
  4. addition2 N aq. NaOH-solution was added
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with DCM (2×)
  7. dry with materiallayers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-c69bb5762aaa43f19e873cc4c04a9430
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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