Trifluoroacetic acid → HCID 68882170, compound

HRID 1723657Notes

Reaction equation

HRID 1723657 reaction equation
C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[CH:16]1([CH2:19][N:20]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([S:38](=[O:49])(=[O:48])[N:39]([CH2:44][CH2:45][O:46][CH3:47])C(C)(C)C)=[CH:34][CH:33]=4)[N:26]=3)=[CH:23][N:22]=[C:21]2[CH2:50][CH3:51])[CH2:18][CH2:17]1>>[CH:16]1([CH2:19][N:20]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]4[CH:33]=[CH:34][C:35]([S:38](=[O:48])(=[O:49])[NH:39][CH2:44][CH2:45][O:46][CH3:47])=[CH:36][CH:37]=4)[N:26]=3)=[CH:23][N:22]=[C:21]2[CH2:50][CH3:51])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 68881504HCID 68881504, compound

Product 1

HCID 68882170HCID 68882170, compoundYield 48%

Procedure

Anisole (4.57 ml) followed by trifluoroacetic acid (22 ml) was added to 4-(1-cyclopropylmethyl-2-ethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)-N-(t-butyl)sulphamoyl]anilino}pyrimidine (Method 76; 3.7 g, 7.22 mmol). The mixture was stirred at ambient temperature for two hours, the volatiles were evaporated and the residue dissolved in water and then extracted with EtOAc. The aqueous layer was neutralised with saturated aqueous sodium hydrogen carbonate solution and extracted with EtOAc. The extract was dried and the solvent removed by evaporation. The residue was purified by chromatography on silica gel eluting with EtOAc/MeOH (100:0 increasing in polarity to 98:2) to give the title compound (1.58 g, 48%) as a foam. NMR: 0.00-0.02 m, 2H), 0.18-0.20 m, 2H), 0.86-0.90 (m, 1H), 1.10 (t, 3H), 2.60 (q, 2H), 2.75 (q, 2Hy, 3.01 (s, 3H>, 3.18 (q, 2H), 4.40 (d, 2H), 7.10 (d, 1H), 7.35 (t, 1H), 7.52 (s, 1H), 7.57 (d, 2H), 7.77 (d, 2H), 8.30 (d, 1H), 9.70 (s, 1H); m/z 457.

Workup

  1. customthe volatiles were evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with EtOAc
  4. extractionextracted with EtOAc
  5. customThe extract was dried
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by chromatography on silica gel eluting with EtOAc/MeOH (100:0 increasing in polarity to 98:2)

Sources & evidence

ORD record
ord-fb944b13e7fd47018c20ffbaa4e63877
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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