Trifluoroacetic acid → N-[4-(6-{2-[(Piperidin-4-ylmethyl)-amino]-4-trifluoromethyl-phenyl}-pyrimidin-4-yloxy)-benzothiazol-2-yl]-acetamide

HRID 2055987Notes

Reaction equation

HRID 2055987 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[C:26]2[CH:31]=[C:30]([O:32][C:33]3[C:38]4[N:39]=[C:40]([NH:42][C:43](=[O:45])[CH3:44])[S:41][C:37]=4[CH:36]=[CH:35][CH:34]=3)[N:29]=[CH:28][N:27]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[CH:18][C:17]=2[C:26]2[N:27]=[CH:28][N:29]=[C:30]([O:32][C:33]3[C:38]4[N:39]=[C:40]([NH:42][C:43](=[O:45])[CH3:44])[S:41][C:37]=4[CH:36]=[CH:35][CH:34]=3)[CH:31]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 218651314-({2-[6-(2-Acetylamino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21865312N-[4-(6-{2-[(Piperidin-4-ylmethyl)-amino]-4-trifluoromethyl-phenyl}-pyrimidin-4-yloxy)-benzothiazol-2-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-({2-[6-(2-acetylamino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenylamino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester, (Example 160), (0.20 g, 0.30 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (30 mL, Aldrich). The reaction mixture was allowed to stir for 3 h at room temperature and then concentrated in vacuum. The residue was dissolved in EtOAc (30 mL), washed with satd NaHCO3 (2×30 mL), dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (2:1, EtOAc:hexanes) afforded the title compound as yellow film. MS (ESI, pos. ion) m/z: 543 (M+1).

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved in EtOAc (30 mL)
  3. washwashed with satd NaHCO3 (2×30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customPurification by silica gel chromatography (2:1, EtOAc:hexanes)

Sources & evidence

ORD record
ord-29da1a564aba466cae23c93c0916b34d
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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