Sodium Bicarbonate → HCID 135828236, compound

HRID 1784902Notes

Reaction equation

HRID 1784902 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([SH:19])[N:3]=1.[CH3:20][NH:21][C:22](=[O:25])[CH2:23]Br.C([O-])(O)=O.[Na+].C(Cl)Cl.CO>CN(C)C=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:19][CH2:23][C:22]([NH:21][CH3:20])=[O:25])[C:5]([C:17]#[N:18])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[C:7]=1[C:8]#[N:9]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 154907452-Bromo-N-methylacetamideHCID 21226129Dichloromethane methanolHCID 178510481HCID 178510481, compound

Product 1

HCID 135828236HCID 135828236, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature (RT), 53.6 mg (0.2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 45.6 mg (0.3 mmol) of N-methylbromo-acetamide are stirred in 0.5 ml of dimethylformamide (DMF) together with 33.6 mg (0.4 mmol) of NaHCO3 for 4 hours. Thin-layer chromatography (TLC) (CH2Cl2/CH3OH 10:1) shows complete conversion. The entire mixture is diluted with water and ethyl acetate (EA) and the EA phase is dried with MgSO4 and concentrated under reduced pressure. The residue crystallizes from methanol.

Workup

  1. dry with materialthe EA phase is dried with MgSO4
  2. concentrationconcentrated under reduced pressure
  3. customThe residue crystallizes from methanol

Sources & evidence

ORD record
ord-09d8927eed9d4206824edc5084cae123
Source dataset
uspto-grants-2009_03
Patent number
US07504421B2

Reaction notes

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