Trifluoroacetic acid → HCID 121393726, compound

HRID 1480027Notes

Reaction equation

HRID 1480027 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][N:8]1[C:12]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[N:16]=[CH:15][CH:14]=2)=[C:11]([CH3:26])[N:10]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[C:9]1=[O:37])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([N:17]2[C:13]([C:12]3[N:8]([CH2:7][C:6]([OH:38])=[O:5])[C:9](=[O:37])[N:10]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=4)[C:11]=3[CH3:26])=[CH:14][CH:15]=[N:16]2)=[CH:19][CH:20]=1)#[N:25]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 121429617HCID 121429617, compound

Product 1

HCID 121393726HCID 121393726, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-{5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-1-yl}acetate (Example 20) (75 mg, 0.143 mmol) was stirred in DCM (3 mL) and water (0.03 mL). To this mixture was added TFA (0.1 mL) and the mixture stirred overnight. Reaction was incomplete so further TFA (0.5 mL) was added and after 1 h 30 minutes, a further 1 ml was added. After 4 h reaction was complete, solvents were evaporated and the residue partitioned between EtOAc and water. The organic phase was separated, dried over Na2SO4 and evaporated to give the title compound as a gum.

Workup

  1. customReaction
  2. additionwas added and after 1 h 30 minutes
  3. additiona further 1 ml was added
  4. customAfter 4 h reaction
  5. customsolvents were evaporated
  6. customthe residue partitioned between EtOAc and water
  7. customThe organic phase was separated
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-29c5ee335fc14bf19c4dde4a1206a0d7
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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