Morpholine-4-sulfonyl chloride → HCID 57843460, compound

HRID 734963Notes

Reaction equation

HRID 734963 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]2[CH:18]=[C:19]([NH2:23])[CH:20]=[N:21][CH:22]=2)=[CH:12][CH:11]=3)[CH:4]=[N:3]1.[N:24]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]2[CH:18]=[C:19]([NH:23][S:30]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)(=[O:32])=[O:31])[CH:20]=[N:21][CH:22]=2)=[CH:12][CH:11]=3)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 12798265Morpholine-4-sulfonyl chlorideHCID 578434745-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinamine

Product 1

HCID 57843460HCID 57843460, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an oven-dried flask under nitrogen, a solution of 5-[3-(1-methyl-1H-pyrazol-4-yl)-6-quinoxalinyl]-3-pyridinamine (99 mg, 0.327 mmol) in pyridine (3 mL) at room temperature was treated with morpholine-4-sulfonyl chloride (96 mg, 0.491 mmol) by syringe. The reaction was stirred at room temperature for 16.5 hours. The reaction was very sluggish so the reaction was placed in an oil bath at 50° C. and stirred at that temperature for 23 hours. The reaction was progressing to the desired product as determined by LCMS but was not yet complete. The reaction mixture was stirred for an additional 4 days at 50° C. The reaction did not progress to completion. The reaction was cooled to room temperature and concentrated in vacuo. The residue was taken up into 200 mL ethyl acetate and 50 mL water. The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL) followed by brine (100 mL), dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography eluting with 0-10% methanol in dichloromethane provided the desired product as a residue which was not pure. Addition of dichloromethane/ether resulted in precipitate formation. The precipitate was collected by filtration. Recrystallization of the precipitate from ethanol provided the title compound (26 mg, 18%) as a rust-coloured solid. MS(ES)+ m/e 452.0 [M+H]+.

Workup

  1. customwas placed in an oil bath at 50° C.
  2. stirringstirred at that temperature for 23 hours

Sources & evidence

ORD record
ord-5524b4bd4497405d8d52e58c567ca882
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

Loading…