Trifluoroacetic acid → HCID 135729082, compound

HRID 859030Notes

Reaction equation

HRID 859030 reaction equation
FC(F)(F)C(O)=O.COC[O:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[C:22]1[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]2[C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=[CH:31][CH:30]=2)[CH:23]=1>ClCCl>[OH:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[CH:14][C:13]=1[C:22]1[N:27]=[CH:26][N:25]=[C:24]([O:28][C:29]2[C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=[CH:31][CH:30]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21865184HCID 21865184, compound

Product 1

HCID 135729082HCID 135729082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.10 mL, 1.3 mmol, Aldrich) was added dropwise to a solution of N-{4-[6-(2-methoxymethoxy-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide, (Example 136(b)), (0.50 g, 1.0 mmol) in dichloromethane (10 mL) with stirring and cooling in an ice bath. The reaction mixture was stirred for 16 h at room temperature, diluted with dichloromethane (5 mL) and quenched with satd sodium bicarbonate solution. The reaction mixture was diluted with water (100 mL), extracted with dichloro-methane (2×100 mL), and the combined organic extracts were concentrated in vacuum. The resulting white solid was suspended in MeOH (50 mL), collected by filtration, and dried under vacuum to obtain the title compound as a white solid. Mp: 302–304° C. MS (ESI, pos. ion.) m/z: 445 (M+1).

Workup

  1. temperaturecooling in an ice bath
  2. stirringThe reaction mixture was stirred for 16 h at room temperature
  3. customquenched with satd sodium bicarbonate solution
  4. additionThe reaction mixture was diluted with water (100 mL)
  5. extractionextracted with dichloro-methane (2×100 mL)
  6. concentrationthe combined organic extracts were concentrated in vacuum
  7. filtrationcollected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-1aaedeeb3aa142cf982566689e4c1fda
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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