Water → HCID 178512366, compound

HRID 1059456Notes

Reaction equation

HRID 1059456 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][NH:16][C:17](=[NH:20])SC)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[N:21]#[C:22][NH2:23].O.C(OCC)(=O)C>CN(C)C=O>[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][NH:16][C:17]([NH2:20])=[N:23][C:22]#[N:21])[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9864CyanamideHCID 178504028HCID 178504028, compound

Product 1

HCID 178512366HCID 178512366, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

450 mg of N-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-S-methylisothiourea and 500 mg of cyanamide were heated in 30 ml of N,N-dimethylformamide to 70° C. for 12 hours. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The organic layer was extracted and washed with water. After adding 5 g of silica gel, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia) to thereby give 340 mg of the title compound as yellow crystals.

Workup

  1. customwas brought back to room temperature
  2. extractionThe organic layer was extracted
  3. washwashed with water
  4. additionAfter adding 5 g of silica gel
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record
ord-c985b0f7246b43c580c8bfeafc85446c
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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