2-bromo-N,N-diethylacetamide → HCID 135828231, compound

HRID 720450Notes

Reaction equation

HRID 720450 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.[CH2:20]([N:22]([CH2:27][CH3:28])[C:23](=[O:26])[CH2:24]Br)[CH3:21].C([O-])(O)=O.[Na+].C(Cl)Cl.CO>CN(C=O)C.O.C(OCC)(=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:19][CH2:24][C:23]([N:22]([CH2:27][CH3:28])[CH2:20][CH3:21])=[O:26])[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 2255452-bromo-N,N-diethylacetamideHCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 178510481HCID 178510481, compound

Product 1

HCID 135828231HCID 135828231, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At RT, 53.6 mg (0.2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 58.2 mg (0.3 mmol) of N,N-diethylbromoacetamide are stirred in 0.5 ml of DMF together with 33.6 mg (0.4 mmol) of NaHCO3 for 4 hours. TLC (CH2Cl2/CH3OH 10:1) shows complete conversion. The entire mixture is diluted with water and ethyl acetate 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-57c24c9c4d4b4f118c2b63c439fffa3e
Source dataset
uspto-grants-2006_11
Patent number
US07135486B1

Reaction notes

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