Water → HCID 135828225, compound

HRID 720453Notes

Reaction equation

HRID 720453 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]([S:19][CH2:20][CH2:21][NH2:22])[N:3]=1.[C:23](N1C=CN=C1)(=[O:25])[CH3:24].O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])[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

5

Reactant 3

HCID 962WaterHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 135828224HCID 135828224, compound

Product 1

HCID 135828225HCID 135828225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At RT 60 mg (0.2 mmol) of 2-amino-6-[(2-aminoethyl)sulfanyl]-4-(4-hydroxyphenyl)-3,5-pyridinedicarbonitrile and 30 mg (0.3 mmol) of N-acetylimidazole are stirred in 0.5 ml of DMF for 1 hour. Water is slowly added dropwise, the mixture becomes slightly turbid and the crude product crystallizes out. The product is filtered off with suction, washed with water and dried under reduced pressure. This gives 53 mg of yellow crystals. The crystals are dissolved in 1 ml of a 1:1 mixture of CH2Cl2/CH3OH, and a few drops of concentrated ammonia are added (removal of diacetylated byproduct). The mixture is stirred at RT for 5 hours. The product crystallizes out when the reaction solution is concentrated. The product is filtered off with suction and washed with methanol.

Workup

  1. customthe crude product crystallizes out
  2. filtrationThe product is filtered off with suction
  3. washwashed with water
  4. customdried under reduced pressure
  5. dissolutionThe crystals are dissolved in 1 ml of a 1:1 mixture of CH2Cl2/CH3OH, and a few drops of concentrated ammonia
  6. additionare added
  7. custom(removal of diacetylated byproduct)
  8. customThe product crystallizes out when the reaction solution
  9. concentrationis concentrated
  10. filtrationThe product is filtered off with suction
  11. washwashed with methanol

Sources & evidence

ORD record
ord-bc48abbcbe4340d7aa468ad9f54d782b
Source dataset
uspto-grants-2006_11
Patent number
US07135486B1

Reaction notes

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