Trifluoroacetic acid → HCID 25105788, compound

HRID 1675344Notes

Reaction equation

HRID 1675344 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH2:14]1[C:18]2[CH2:19][NH:20][CH2:21][C:17]=2[CH2:16][N:15]1[C:22]1[S:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:26]=1.FC(F)(F)C(O)=O.C(N(CC)CC)C>C(Cl)Cl.N1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:20]1[CH2:21][C:17]2[CH2:16][N:15]([C:22]3[S:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:26]=3)[CH2:14][C:18]=2[CH2:19]1)=[O:6]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 58459772HCID 58459772, compound

Product 1

HCID 25105788HCID 25105788, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2-Trifluoromethylbenzoyl chloride (50.4 mg, 0.24 mmol) was added at RT to ethyl 2-(3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrol-2-yl)thiazole-5-carboxylate; trifluoroacetic acid salt (60 mg, 0.16 mmol) and triethylamine (64 μl, 0.46 mmol) in 4 ml of methylene chloride and 2 ml of pyridine. After 3 h at RT, the mixture was concentrated, water and ethyl acetate were added, and the organic phase was removed, concentrated by evaporation and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 63 mg (91%), M+H+: 438.04.

Workup

  1. concentrationthe mixture was concentrated
  2. additionwater and ethyl acetate were added
  3. customthe organic phase was removed
  4. concentrationconcentrated by evaporation
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-af505f2567b242e4ba26e47593374de4
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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