Water → HCID 16070572, compound

HRID 1710720Notes

Reaction equation

HRID 1710720 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH2:19])[C:9]([NH2:18])=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.Cl.[C:21](Cl)(=O)[C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1.O>N1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]2[NH:19][C:21]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:18][C:9]2=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 59457625HCID 59457625, compound

Product 1

HCID 16070572HCID 16070572, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(2-furyl)-6-pyridin-4-ylpyrazine-2,3-diamine (Example 87, 146 mg, 0.58 mmol) and nicotinoyl chloride hydrochloride (516 mg, 2.9 mmol) in pyridine (5 mL) was stirred and heated at reflux for 24 h. Then polyphosphoric acid was added and the stirring was continued at the same temperature for 24 h. The reaction was allowed to cool to room temperature and was poured into water and extracted with ethyl acetate. The organic phase was dried (MgSO4), evaporated and the residue was purified by silica gel chromatography (CH2Cl2/MeOH/NH3 50:8:1). The appropriate fractions were concentrated to leave a solid which upon washing with diethyl ether give the title compound as a light brown solid (82 mg, 61%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customthe residue was purified by silica gel chromatography (CH2Cl2/MeOH/NH3 50:8:1)
  7. concentrationThe appropriate fractions were concentrated
  8. customto leave a solid which
  9. washupon washing with diethyl ether

Sources & evidence

ORD record
ord-72dc350838b64f72862b246c6b7ac2c1
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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