N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide → 4-amino-N-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamide

HRID 1585699Notes

Reaction equation

HRID 1585699 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24]C(=O)C)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:4]=1>[OH-].[Na+]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C:5]2[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[N:6]=2)(=[O:16])=[O:17])=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 54406992N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

Product 1

HCID 104278424-amino-N-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamideYield 30.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.30 g (0.00077 mol) of N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide was boiled at reflux in 30 ml of 1N aqueous sodium hydroxide for 3 hours. The mixture was cooled and extracted with ethyl acetate. Crystals then separated from the aqueous phase and, after suction filtration, were chromatographed over silica gel with ethyl acetate/ethanol 9:1 as the eluent. There was obtained 0.082 g (30%) of 4-amino-N-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p. 299-301° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customCrystals then separated from the aqueous phase
  4. filtrationafter suction filtration
  5. customwere chromatographed over silica gel with ethyl acetate/ethanol 9:1 as the eluent

Sources & evidence

ORD record
ord-b3bc7d8e654a4642ad96ef8550e71b63
Source dataset
uspto-grants-1999_08
Patent number
US05939451

Reaction notes

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