Water → HCID 54099599, compound

HRID 1903804Notes

Reaction equation

HRID 1903804 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.NC[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][CH2:15][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][C:9]([F:12])=[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 27247922-[(4-Fluorophenoxy)methyl]oxiraneHCID 12818868HCID 12818868, compound

Product 1

HCID 54099599HCID 54099599, compound

Procedure

3.36 g. 4-Fluorophenyl glycidyl ether and 7.0 g. 4-(2-aminoethylamino)-indazole are dissolved in 10 ml. dimethylformamide and left to stand for 2 days at ambient temperature. The reaction mixture is then poured into water, extracted with methylene chloride, dried and purified chromatographically on silica gel in the manner described in Example 24. The residue of the pure fractions is taken up in ethyl acetate, then mixed with 2 g. benzoic acid, filtered off with suction and recrystallized from isopropyl alcohol, with the use of active charcoal. There are obtained 5.6 g. (60% of theory) of the desired product in the form of colorless crystals; m.p. 157°-159° C.

Workup

  1. extractionextracted with methylene chloride
  2. customdried
  3. custompurified chromatographically on silica gel in the manner
  4. additionmixed with 2 g
  5. filtrationbenzoic acid, filtered off with suction
  6. customrecrystallized from isopropyl alcohol, with the use of active charcoal
  7. customThere are obtained 5.6 g

Sources & evidence

ORD record
ord-1665adeda1a444069c0d97ac6d09768c
Source dataset
uspto-grants-1984_03
Patent number
US04438128

Reaction notes

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