Methanol → HCID 69310469, compound

HRID 2117748Notes

Reaction equation

HRID 2117748 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][C:6]1[N:7]([CH2:32][CH2:33][CH3:34])[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:31])(=[O:30])[NH:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:20][CH:19]=3)[N:12]=2)=[CH:9][N:10]=1.[CH3:35]O>>[CH3:1][S:2][CH2:5][C:6]1[N:7]([CH2:32][CH2:33][CH3:34])[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:31])(=[O:30])[NH:25][CH2:26][CH2:27][O:28][CH2:29][CH3:35])=[CH:20][CH:19]=3)[N:12]=2)=[CH:9][N:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4378561Sodium methanethiolateHCID 69310470HCID 69310470, compound

Product 1

HCID 69310469HCID 69310469, compound

Procedure

Sodium thiomethoxide (21 mg, 0.3 mmol) was added to a stirred solution of 4-[2-(chloromethyl)-1-(propyl)imidazol-5-yl]-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Method 116; 52 mg, 0.1 mmol) in MeOH (5 ml) and the solution was stirred at ambient temperature for 3 hour. The solvent was removed evaporation and the residue was partitioned between water and EtOAc. The organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (Na2SO4) and the volatiles removed by evaporation. The residue was triturated with ether and collected by filtration. This solid was suspended in MeOH (2 ml) and 1.0M ethereal hydrogen chloride was added to give a clear solution. The volatiles were removed by evaporation and the residue triturated with ether giving the title compound (42 mg, 80%) as the hydrochloride salt. NMR: 0.72 (t, 3H), 1.06 (t, 3H), 1.63 (m, 2H), 2.18 (s, 3H), 2.88 (q, 2H), 3.35 (m, 4H), 4.42 (s, 2H), 4.72 (m, 2H), 7.37 (d, 1H), 7.54 (t, 1H), 7.75 (d, 2H), 7.89 (d, 2H), 8.39 (s, 1H), 8.68 (d, 1H), 10.14 (s, 1H); m/z 491.

Workup

  1. customThe solvent was removed
  2. customevaporation
  3. customthe residue was partitioned between water and EtOAc
  4. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried (Na2SO4)
  6. customthe volatiles removed by evaporation
  7. customThe residue was triturated with ether
  8. filtrationcollected by filtration
  9. addition1.0M ethereal hydrogen chloride was added
  10. customto give a clear solution
  11. customThe volatiles were removed by evaporation
  12. customthe residue triturated with ether giving the title compound (42 mg, 80%) as the hydrochloride salt

Sources & evidence

ORD record
ord-dfea34a1af074a3c8f109e296e2f19a2
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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