Trifluoroacetic acid → HCID 10474988, compound

HRID 857672Notes

Reaction equation

HRID 857672 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[C:22]([O:24][C:25]2[CH:34]=[C:33]3[C:28]([CH:29]=[CH:30][CH:31]=[N:32]3)=[CH:27][CH:26]=2)[N:21]=[CH:20][N:19]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:32]1[C:33]2[C:28](=[CH:27][CH:26]=[C:25]([O:24][C:22]3[N:21]=[CH:20][N:19]=[C:18]([C:9]4[CH:10]=[CH:11][C:12]([C:14]([F:16])([F:15])[F:17])=[CH:13][C:8]=4[NH2:7])[CH:23]=3)[CH:34]=2)[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58759743HCID 58759743, compound

Product 1

HCID 10474988HCID 10474988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a round-bottom flask was added {2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester, (Example 162), (3.2 g, 6.6 mmol) and CH2Cl2 (100 mL). The mixture was cooled to 0° C. and trifluoroacetic acid (25 mL) was added. After stirring for 5 min at 0° C., the mixture was allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was concentrated in vacuum and diluted with CH2Cl2 (200 mL) and satd NaHCO3 (200 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (100 mL). The combined extracts were washed with aq NaHCO3 (20% satd NaHCO3/H2O), H2O, brine and then dried over Na2SO4, filtered and concentrated onto silica gel. Purification by silica gel chromatography (gradient, 40 to 75% EtOAc/hexanes) afforded the title compound as a yellow solid. Mp: 193–194° C. MS (ESI, pos. ion) m/z: 383.2 (M+1).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuum
  4. additiondiluted with CH2Cl2 (200 mL) and satd NaHCO3 (200 mL)
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (100 mL)
  7. washThe combined extracts were washed with aq NaHCO3 (20% satd NaHCO3/H2O), H2O, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated onto silica gel
  11. customPurification by silica gel chromatography (gradient, 40 to 75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9251c83bea4b4caaa125123c6f1b10d1
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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