Trifluoroacetic acid → HCID 86698463, compound

HRID 527676Notes

Reaction equation

HRID 527676 reaction equation
[CH3:1][C@:2]([NH:26]C(=O)OC(C)(C)C)([C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]([CH3:25])[CH2:18][CH2:19][O:20]3)=[N:12][CH:13]=1)=[O:6])[CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:25][CH:17]1[C:16]2[C:21](=[CH:22][CH:23]=[CH:24][C:15]=2[O:14][C:11]2[N:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C@:2]([CH3:1])([CH2:3][CH3:4])[NH2:26])=[CH:9][N:10]=2)[O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698461HCID 86698461, compound2×

Product 1

HCID 86698463HCID 86698463, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {(1R)-1-methyl-1-[({2-[(4-methyl-3,4-dihydro-2H-chromen-5-yl)oxy]-5-pyrimidinyl}amino)carbonyl]propyl}carbamate (Intermediate 218, 100 mg, 0.219 mmol) in dry Dichloromethane (5 mL), cooled to 0° C., TFA (1 mL, 12.98 mmol) was added dropwise. The reaction mixture was stirred at that temperature for 3 hours, then it was allowed to reach the room temperature and stirred at that temperature for 2 hours. Volatiles were evaporated and the residue was diluted with DCM (10 mL) and washed with an aqueous saturated solution of NaHCO3 (10 mL). The organic layer was separated, dried (Na2SO4), filtered and evaporated to afford the title compound (78 mg) as white solid that was used in the next step without further purification.

Workup

  1. customthe room temperature
  2. stirringstirred at that temperature for 2 hours
  3. customVolatiles were evaporated
  4. additionthe residue was diluted with DCM (10 mL)
  5. washwashed with an aqueous saturated solution of NaHCO3 (10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-910231f0819242738aa996f4f566ea6e
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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