Ethylamine → HCID 17774540, compound

HRID 610809Notes

Reaction equation

HRID 610809 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]([N:19]3[CH2:22][CH2:21][CH2:20]3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:23]([NH2:25])[CH3:24]>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]([NH:25][CH2:23][CH3:24])[N:15]=[C:14]([N:19]3[CH2:22][CH2:21][CH2:20]3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 10807034HCID 10807034, compound

Product 1

HCID 17774540HCID 17774540, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
130 °C

Procedure

0.2 g (0.00061 mol) of 4-amino-N-(2-azetidin-1-yl-6-chloro-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 20 ml of ethanol, treated with 3.9 ml (0.061 mol) of ethylamine and stirred in an autoclave at 130° C. for 12 hours. The reaction mixture was free from solvent, the residue was suspended in 5 ml of ethanol and treated in an ultrasound bath for 15 minutes. The precipitate was filtered off, dissolved in 10 ml of 0.1N NaOH and filtered. The filtrate was adjusted to pH 6 with 0.1N HCl. The precipitate was filtered off under suction, washed with water and dried. There was obtained 0.090 g (44%) of 4-amino-N-(2-azetidin-1-yl-6-ethylamino-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p.: 260-262° C.

Workup

  1. additiontreated in an ultrasound bath for 15 minutes
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in 10 ml of 0.1N NaOH
  4. filtrationfiltered
  5. filtrationThe precipitate was filtered off under suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e48d167610f04b43a5c6c550662f46ac
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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