Water → HCID 69309054, compound

HRID 2117751Notes

Reaction equation

HRID 2117751 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].Cl[CH2:7][C:8]1[N:9]([CH2:35][CH2:36][CH3:37])[C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:34])(=[O:33])[NH:27][CH2:28][CH2:29][O:30][CH2:31][CH3:32])=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:12]=1.O>C(O)(C)C>[CH:2]([O:3][CH2:7][C:8]1[N:9]([CH2:35][CH2:36][CH3:37])[C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([S:26](=[O:34])(=[O:33])[NH:27][CH2:28][CH2:29][O:30][CH2:31][CH3:32])=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][N:12]=1)([CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 109204432-Propanol, sodium salt (1:1)HCID 69310476HCID 69310476, compound

Product 1

HCID 69309054HCID 69309054, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium isopropoxide (87 mg, 1.05 mmol) was added to a stirred suspension of 4-[2-(chloromethyl)-1-(propyl)imidazol-5-yl]-2-{4-[N-(2-ethoxyethyl)sulphamoyl]anilino}pyrimidine (Method 116; 100 mg, 0.21 mmol) in isopropanol (20 ml). The reaction was stirred for 48 hours at ambient temperature, and was then poured into water (80 ml) and extracted with EtOAc (3×30 ml). The extracts were combined washed with brine (2×40 ml), dried and the volatiles removed by evaporation. The residue was purified by reverse phase HLPC (C18 column) eluting with aqueous ammonia/water/acetonitrile (5:90:5 decreasing in polarity to (5:0:95) to give the title compound (18 mg, 17%) as a brown gum. M/z 503.

Workup

  1. extractionextracted with EtOAc (3×30 ml)
  2. washThe extracts were combined washed with brine (2×40 ml)
  3. customdried
  4. customthe volatiles removed by evaporation
  5. customThe residue was purified by reverse phase HLPC (C18 column)
  6. washeluting with aqueous ammonia/water/acetonitrile (5:90:5 decreasing in polarity to (5:0:95)

Sources & evidence

ORD record
ord-c926989a6dd14e7cae3eb5802f344c53
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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