4-Methylmorpholine → HCID 21218514, compound

HRID 1585473Notes

Reaction equation

HRID 1585473 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13]([C:17]([OH:19])=O)[N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH2:23].CN1CCOCC1>ClCCl.C(OCC)C>[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH:23][C:17]([C:13]1[N:12]=[C:11]([S:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:16]=[N:15][CH:14]=1)=[O:19]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 97092,4-DifluoroanilineHCID 21218515HCID 21218515, compound

Product 1

HCID 21218514HCID 21218514, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

7 g (11 mmol) of a 50% strength solution of propanephosphonic anhydride in dichloromethane are added to a solution of 2.8 g (10 mmol) of 2-(3-nitrophenylthio)-6-pyrazinecarboxylic acid, 3.2 g (25 mmol) of 2,4-difluoroaniline and 3 g (30 mmol) of 4-methylmorpholine in dichloromethane at 0° C. The reaction mixture is heated to room temperature. After 12 hours, the solvent is istilled off under reduced pressure. The residue is taken up in diethyl ether and the solution is extracted with 10% strength, aqueous hydrochloric acid, washed with distilled water and with saturated, aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 4/1 (v/v)). Yield 1.6 g (40%); light yellow, crystalline solid, mp. 131-135° C.

Workup

  1. extractionthe solution is extracted with 10% strength, aqueous hydrochloric acid
  2. washwashed with distilled water
  3. dry with materialwith saturated, aqueous sodium bicarbonate solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 4/1 (v/v))

Sources & evidence

ORD record
ord-ccbc99721d2c499c8ab16d69d754835d
Source dataset
uspto-grants-1999_08
Patent number
US05939359

Reaction notes

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