Trifluoroacetic acid → HCID 67966823, compound

HRID 527607Notes

Reaction equation

HRID 527607 reaction equation
CC([N:5]([C:9]([CH3:32])([CH3:31])[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][C:20]2[C:25]3[C:26]([CH3:30])([CH3:29])[CH2:27][O:28][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[N:17][CH:18]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:29][C:26]1([CH3:30])[C:25]2[C:20]([O:19][C:16]3[N:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[C:9]([CH3:32])([CH3:31])[NH2:5])=[CH:14][N:15]=3)=[CH:21][CH:22]=[CH:23][C:24]=2[O:28][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698443HCID 86698443, compound2×

Product 1

HCID 67966823HCID 67966823, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[2-({2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinyl}amino)-1,1-dimethyl-2-oxoethyl]carbamate (Intermediate 142, 30 mg, 0.068 mmol) in dry Dichloromethane (DCM) (1.6 mL) at 0° C. TFA (0.4 ml, 5.19 mmol) was slowly added and the reaction mixture was stirred for 1 h at the same temperature. The solvent and the excess of TFA were evaporated end the residue was dissolved in DCM (5 ml) and an aqueous saturated solution of NaHCO3 was added while the pH was allowed to reach ˜8-9. Two phases were separated and the organic layer was dried (Na2SO4), filtered and evaporated affording the title compound (20 mg) as a white solid.

Workup

  1. customat 0° C
  2. customThe solvent and the excess of TFA were evaporated end the residue
  3. dissolutionwas dissolved in DCM (5 ml)
  4. additionan aqueous saturated solution of NaHCO3 was added while the pH
  5. customTwo phases were separated
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d555aa377a554591a173dc88d53933f4
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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