Water → HCID 54441944, compound

HRID 365206Notes

Reaction equation

HRID 365206 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.NC[CH2:14][CH2:15][NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][NH:21]2.C[N:27]([CH3:30])[CH:28]=O.[OH2:31]>>[C:3]([O:4][CH:2]([CH2:30][NH:27][CH2:28][CH2:14][CH2:15][NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[N:20][NH:21]2)[CH2:1][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:31])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 31217Phenyl glycidyl etherHCID 19354427HCID 19354427, compound

Product 1

HCID 54441944HCID 54441944, compound

Procedure

3.0 g. Phenyl glycidyl ether and 7.5 g. 4-(3-aminopropylamino)-indazole are dissolved in 10 ml. dimethylformamide at 60° C. and then left to stand for a day at ambient temperature. The reaction mixture is poured into water, extracted with methylene chloride, dried and purified chromatographically on silica gel in the manner described in Example 21. The viscous residue of the pure fractions (5.3 g.; 78% of theory) is dissolved in a little ethyl acetate, whereafter 2 g. benzoic acid are added thereto, followed by suction filtration and recrystallization from ethanol, with the use of active charcoal. There are obtained 2.8 g. (30% of theory) of the desired product in the form of colorless crystals; m.p. 162°-164° C.

Workup

  1. waitto stand for a day at ambient temperature
  2. extractionextracted with methylene chloride
  3. customdried
  4. custompurified chromatographically on silica gel in the manner
  5. dissolutionThe viscous residue of the pure fractions (5.3 g.; 78% of theory) is dissolved in a little ethyl acetate, whereafter 2 g
  6. additionbenzoic acid are added
  7. filtrationfollowed by suction filtration and recrystallization from ethanol, with the use of active charcoal
  8. customThere are obtained 2.8 g

Sources & evidence

ORD record
ord-eacd0e37ecb04c42833bcf65b4c6cb23
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

Loading…