Trifluoroacetic acid → HCID 58095014, compound

HRID 2282331Notes

Reaction equation

HRID 2282331 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH:23]C(C)(C)C)[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])[CH:2]=[CH2:3].FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH2:23])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 58095024HCID 58095024, compound

Product 1

HCID 58095014HCID 58095014, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl]-N-(tert-butyl)[1,3]thiazolo[5,4-d]pyrimidin-2-amine (480 mg, 0.886 mmol), trifluoroacetic Acid (2.0 mL) and DCM (6.0 mL) was stirred at rt. After being stirred for 30 min, trifluoromethanesulfonic acid (0.118 mL, 1.33 mmol) was added to the mixture. The mixture was stirred at rt for 49 hours and then the solvent was removed in vacuo. To the residue, sat. NaHCO3 and EtOAc were added. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was crystallized from EtOAc and Hexane to yield the title compound (352.9 mg, 82%) as a pale yellow solid. LCMS: (AA) ES+ 485, 487. NMR (400 MHz, d6-DMSO) δ: 8.66 (s, 1H), 8.55 (s, 1H), 8.43 (bs, 2H), 7.74 (d, J=2.0 Hz, 1H), 7.41 (dd, J=8.3, 2.3 Hz, 1H), 7.23-7.20 (m, 2H), 7.02 (d, J=1.3 Hz, 1H), 5.68-5.59 (m, 1H), 5.08-5.05 (m, 1H), 4.85-4.80 (m, 1H), 4.35 (d, J=5.5 Hz, 2H).

Workup

  1. stirringAfter being stirred for 30 min
  2. stirringThe mixture was stirred at rt for 49 hours
  3. customthe solvent was removed in vacuo
  4. additionTo the residue, sat. NaHCO3 and EtOAc were added
  5. stirringAfter being stirred for 30 min
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from EtOAc and Hexane

Sources & evidence

ORD record
ord-da7f6cebcce1414c8c219416e7e95657
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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