Trifluoroacetic acid → HCID 57520094, compound

HRID 1528099Notes

Reaction equation

HRID 1528099 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:35])[NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[CH2:23][CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH:27]=4)[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:25]1[CH2:26][CH:27]=[C:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[NH:11][C:10]([NH:9][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:36])([F:37])[F:1])[N:8]=2)=[O:35])[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57520093HCID 57520093, compound

Product 1

HCID 57520094HCID 57520094, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 g of tert-butyl 4-{4-[3-(6-trifluoromethyl-pyridin-2-yl)-ureido]-quinolin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylate (0.389 mmol) were dissolved in 0.6 ml DCM (yellow solution). 0.300 ml of TFA (3.89 mmol) were added and the reaction mixture was stirred for 2 h at RT. After evaporation of the solvent and excess TFA in vacuum, water was added to the residue, the acidic mixture extracted with ethyl acetate, the water phase adjusted to pH 9 with 1M NaOH and subsequently extracted three times with DCM. The combined DCM solutions were washed with a small amount of brine, dried over sodium sulphate and the solvent was removed in vacuum. 130 mg of the desired product were obtained as light yellow powder (yield: 81%).

Workup

  1. customAfter evaporation of the solvent and excess TFA in vacuum, water
  2. additionwas added to the residue
  3. extractionthe acidic mixture extracted with ethyl acetate
  4. extractionsubsequently extracted three times with DCM
  5. washThe combined DCM solutions were washed with a small amount of brine
  6. dry with materialdried over sodium sulphate
  7. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-e1b7751bd9c0472e9f8a8e0862e1abc4
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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