Trifluoroacetic acid → HCID 69311878, compound

HRID 2117746Notes

Reaction equation

HRID 2117746 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]([CH3:43])=[CH:10][C:11]1[N:12]([CH2:41][CH3:42])[C:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([S:29](=[O:40])(=[O:39])[N:30]([CH2:35][CH2:36][O:37][CH3:38])C(C)(C)C)=[CH:25][CH:24]=3)[N:17]=2)=[CH:14][N:15]=1.C1(OC)C=CC=CC=1>>[CH3:8][C:9]([CH3:43])=[CH:10][C:11]1[N:12]([CH2:41][CH3:42])[C:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([S:29](=[O:39])(=[O:40])[NH:30][CH2:35][CH2:36][O:37][CH3:38])=[CH:27][CH:28]=3)[N:17]=2)=[CH:14][N:15]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 69310496HCID 69310496, compound

Product 1

HCID 69311878HCID 69311878, compoundYield 46.9%

Procedure

Aqueous TFA (90%) was added to a mixture of 4-[2-(2-methylprop-1-enyl)-1-ethylimidazol-5-yl]-2-{4-[N-(2-methoxyethyl)-N-t-butylsulphamoyl]anilino}pyrimidine (Method 111; 70 mg, 0.14 mmol), and anisole (90 μl, 0.83 mmol), and the mixture stirred at ambient temperature for 1 hour. The volatiles were evaporated and the residue dissolved in water. The solution was neutralised (NaHCO3), and extracted with EtOAc. The extracts were dried, and the solvent evaporated to give the title compound (30 mg, 41%). NMR: 1.19 (t, 3H), 1.99 (s, 3H), 2.15 (s, 3H), 2.89 (q, 2H), 3.18 (s, 3H), 3.30-3.28 (m, 2H), 4.65 (q, 2H), 6.28 (s, 1H), 7.25 (d, 1H), 7.50 (t, 1H), 7.70 (d, 2H), 7.85 (s, 1H), 7.89 (d, 2H), 8.45 (d, 1H), 9.85 (s, 1H); m/z: 457.

Workup

  1. customThe volatiles were evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with EtOAc
  4. customThe extracts were dried
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-31aa58cf96a745f49205d88e196e1c1e
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

Loading…