Dichloromethane → HCID 19964159, compound

HRID 977060Notes

Reaction equation

HRID 977060 reaction equation
Cl[S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:15][CH3:16])=[N:9][C:10]([CH3:14])=[CH:11]2)[N:6]=1)(=[O:4])=[O:3].[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26].ClCCl>N1C=CC=CC=1>[CH2:25]([O:24][C:23]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[NH:17][S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:15][CH3:16])=[N:9][C:10]([CH3:14])=[CH:11]2)[N:6]=1)(=[O:4])=[O:3])[CH3:26]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8172524-ethoxypyridin-3-amineHCID 15003653HCID 15003653, compound

Product 1

HCID 19964159HCID 19964159, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chlorosulfonyl-5-methoxy-7-methyl[1,2,4]triazolo[1,5-c]pyrimidine (1.5 g, 5.7 mmol) was added to a solution of 0.8 g (5.7 mmol) of 3-amino-4-ethoxypyridine in 30 mL of dry pyridine in portions over 10 minutes with stirring. After 16 hours the reaction mixture was poured into 400 mL of dichloromethane. The resulting mixture was washed with 150 mL of water, dried over magnesium smlfate, and filtered. The liltrate was combined with 5 g of silica gel and the mixture was concentrated by evaporation under reduced pressure. The resulting silica plug was placed onto a 200 g silica gel column and eluted with dichloromethane containing increasing amount of ethanol. The product fractions were combined and concentrated by evaporation under reduced pressure and the solid obtained was dried to obtain 0.75 g (36 percent of theory) of the title compound as a white solid melting at 184°-186° C.

Workup

  1. washThe resulting mixture was washed with 150 mL of water
  2. dry with materialdried over magnesium smlfate
  3. filtrationfiltered
  4. concentrationthe mixture was concentrated by evaporation under reduced pressure
  5. washeluted with dichloromethane containing
  6. temperatureincreasing amount of ethanol
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customthe solid obtained
  9. customwas dried

Sources & evidence

ORD record
ord-e906353c02b447eb8df170b2dffed763
Source dataset
uspto-grants-1997_03
Patent number
US05614469

Reaction notes

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