Potassium hydroxy sulfite → HCID 69310534, compound

HRID 2117750Notes

Reaction equation

HRID 2117750 reaction equation
OO[S:3]([O-:5])=[O:4].[K+].C(S[CH2:10][C:11]1[N:12]([CH2:38][CH2:39][CH3:40])[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:37])(=[O:36])[NH:30][CH2:31][CH2:32][O:33][CH2:34][CH3:35])=[CH:25][CH:24]=3)[N:17]=2)=[CH:14][N:15]=1)C.CO.[CH3:43][C:44](C)=O.O>O>[CH2:43]([S:3]([CH2:10][C:11]1[N:12]([CH2:38][CH2:39][CH3:40])[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:37])(=[O:36])[NH:30][CH2:31][CH2:32][O:33][CH2:34][CH3:35])=[CH:27][CH:28]=3)[N:17]=2)=[CH:14][N:15]=1)(=[O:5])=[O:4])[CH3:44]

Participants

5

Reactant 3

HCID 23707502Potassium hydroxy sulfiteHCID 69310484HCID 69310484, compoundHCID 86590524Methanol water acetone

Product 1

HCID 69310534HCID 69310534, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (123 mg, 0.2 mmol) was added to a stirred solution of 4-[2-(ethylthiomethyl)-1-(propyl)imidazol-5-yl]-2-{4-[N-(2-ethoxyethyl)sulphamoyl]anilino}pyrimidine (Example 82; 70 mg, 0.14 mmol) in MeOH/acetone/water (15:5:3) (2 ml) at 0-4° C. The solution was allowed to warm to ambient temperature and stirred for 2 hr. The reaction mixture was diluted with water and extracted with EtOAc. The extracts were combined, washed with brine, dried (Na2SO4) and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5) and the purified product triturated with ether to give the title compound (44 mg, 59%). NMR: 0.65 (t, 3H), 1.03 (t, 3H), 1.27 (t, 3H), 1.52 (m, 2H), 2.85 (q, 2H), 3.30 (m, 6H), 4.64 (t, 2H), 4 81 (s, 2H), 7.25 (d, 1H), 7.46 (t, 1H), 7.70 (d, 2H), 7.79 (s, 1H), 7.97 (d, 2H), 8.50 (d, 1H), 9.91 (s, 1H); m/z 537.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe volatiles removed by evaporation
  5. customThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5)
  6. customthe purified product triturated with ether

Sources & evidence

ORD record
ord-8715fff2397141b1892c1f22312fe378
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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