Acetic Acid → HCID 59313084, compound

HRID 2171567Notes

Reaction equation

HRID 2171567 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[H-].[Na+].Cl[C:18]1[N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[CH:21]=[C:20]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[N:19]=1.C(O)(=O)C>CN(C=O)C.O>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:20]1[N:19]=[C:18]([O:11][CH2:10][CH2:9][NH:8][C:6]2[N:7]=[C:2]([NH2:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][CH:5]=2)[N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 22142587HCID 22142587, compoundHCID 59312932HCID 59312932, compound

Product 1

HCID 59313084HCID 59313084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

2-[(6-Amino-5-nitropyridin-2-yl)amino]ethanol (Example 48A) is introduced into DMF (3 ml) at 0° C., and sodium hydride (60% oil dispersion, 15 mg, 0.4 mmol) is added. The mixture is stirred at 0° C. for 10 min. 5-Chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) (125 mg, 0.4 mmol) in DMF (1 ml) is added dropwise, and the reaction mixture is stirred at RT for 12 h. Glacial acetic acid (200 μl) is added, and the reaction mixture is poured into water and extracted with ethyl acetate (3×50 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. The residue is precipitated from acetonitrile, filtered off, washed with acetonitrile and dried. 36 mg (18% of theory) of product are obtained as a solid.

Workup

  1. stirringthe reaction mixture is stirred at RT for 12 h
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue is precipitated from acetonitrile
  7. filtrationfiltered off
  8. washwashed with acetonitrile
  9. customdried
  10. custom36 mg (18% of theory) of product are obtained as a solid

Sources & evidence

ORD record
ord-364628f88e9a410ea55167cdc2d77d52
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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