Dimethyl Sulfoxide → HCID 9871067, compound

HRID 1281708Notes

Reaction equation

HRID 1281708 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=2)[C:17]([NH:19][C:20]2[CH:21]=[C:22]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][N:33]=[C:32](Cl)[CH:31]=3)=[O:29])[CH:23]=[CH:24][C:25]=2[CH3:26])=[O:18])[CH2:9][CH2:8]1.CS(C)=O>O>[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=2)[C:17]([NH:19][C:20]2[CH:21]=[C:22]([NH:27][C:28]([C:30]3[CH:31]=[CH:32][N:33]=[C:34]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:35]=3)=[O:29])[CH:23]=[CH:24][C:25]=2[CH3:26])=[O:18])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 31268PyrrolidineHCID 18422065HCID 18422065, compound

Product 1

HCID 9871067HCID 9871067, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Pyrrolidine (0.3 g) was added to a stirred mixture of N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}-2-chloropyridine-4-carboxamide (0.5 g) and DMSO (5 ml) and the mixture was stirred and heated to 120° C. for 16 hours. The resultant solution was cooled to ambient temperature and poured into water and extracted with methylene chloride. The organic phase was evaporated and the residue was purified by column chromatography on an isolute SCX ion exchange column using a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound (0.014 g); Mass Spectrum: M+H+513.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was evaporated
  3. customthe residue was purified by column chromatography on an isolute SCX ion exchange column
  4. additiona 99:1 mixture of methanol

Sources & evidence

ORD record
ord-ae6d4732631d424d97c1b9303317683a
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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