Trifluoroacetic acid → HCID 70976206, compound

HRID 1505372Notes

Reaction equation

HRID 1505372 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:11][C:12]2[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:14]=[N:13][C:12]([O:11][C:6]2[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[N:17][CH:16]=1)=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71006778HCID 71006778, compound2×

Product 1

HCID 70976206HCID 70976206, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl ((1R)-1-{[(2-{[3-(ethyloxy)-4-methylphenyl]oxy}-5-pyrimidinyl)amino]carbonyl}propyl)carbamate (Intermediate 93, 80 mg) in dichloromethane (1 mL) cooled to 0° C., TFA (573 μl, 7.43 mmol) was added dropwise. The mixture reaction was stirred at 0° C. for 1.5. The solvent and the TFA were evaporated. The mixture was diluted with dichloromethane and an aqueous saturated solution of NaHCO3. The organic layer was separated, dried over sodium sulphate, filtered end evaporated to afford the title compound (65 mg) which was directly used in the next step.

Workup

  1. customThe mixture reaction
  2. customThe solvent and the TFA were evaporated
  3. additionThe mixture was diluted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered end
  7. customevaporated

Sources & evidence

ORD record
ord-2532e0997d634b578360fe29a0b86448
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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