Pyrrolidine → HCID 10760148, compound

HRID 378269Notes

Reaction equation

HRID 378269 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[N:15]=[C:14]([NH:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 108527114-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 10760148HCID 10760148, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.314 g (0.001 mol) of 4-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide and 2.5 ml (0.15 mol) of pyrrolidine were stirred in 20 ml of ethanol in an autoclave at 130° C. for 4 hours. The reaction mixture was freed from solvent, the residue was suspended in 5 ml of ethanol and treated in an ultrasound bath for 15 min. The precipitate was filtered off, dissolved in 150 ml of 1N NaOH and filtered. The filtrate was adjusted to pH 6 with 1N HCl. The precipitate was filtered off under suction, washed with water and dried. There was obtained 0.22 g (63%) of 4 -amino-N-(2-methylamino-6-pyrrolidin-1-yl-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p.: >300° C.

Workup

  1. additiontreated in an ultrasound bath for 15 min
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in 150 ml of 1N NaOH
  4. filtrationfiltered
  5. filtrationThe precipitate was filtered off under suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-71b9a28dd77942ddb15fdf5ed872f699
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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