Sodium periodate → HCID 69310535, compound

HRID 2117749Notes

Reaction equation

HRID 2117749 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([S:9][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)[CH3:8]>O.CO>[CH2:7]([S:9]([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:2])[CH3:8]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 69310484HCID 69310484, compound

Product 1

HCID 69310535HCID 69310535, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium periodate (43 mg, 0.2 mmol) in water (0.5 ml) 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 (2 ml) and the solution was stirred for 18 hours. The MeOH was removed by evaporation and the aqueous residue was extracted with EtOAc. The extracts were combined, washed with brine, dried and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10) and the purified product triturated with ether to give the title compound (37 mg, 51%). NMR: 0.68 (t, 3H), 1.05 (t, 3H), 1.22 (t, 3H), 1.52 (m, 2H), 2.85 (m, 4H), 3.33 (m, 4H), 4.31 (d of d, 2H), 4.63 (m, 2H), 7.23 (d, 1H), 7.46 (t, 1H), 7.70 (d, 2H), 7.78 (s, 1H), 7.86 (d, 2H), 8.48 (d, 1H), 9.90 (s, 1H); m/z 521.

Workup

  1. customThe MeOH was removed by evaporation
  2. extractionthe aqueous residue was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. customthe volatiles removed by evaporation
  6. customThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10)
  7. customthe purified product triturated with ether

Sources & evidence

ORD record
ord-71687a7d790746ab91efa3ad00085a3a
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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