Water → 1-Phenoxy-3-[2-(5-methylindazol-4-ylamino)-ethylamino]-propan-2-ol benzoate

HRID 365209Notes

Reaction equation

HRID 365209 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.[CH3:12][C:13]1[C:14]([NH:22][CH2:23]CN)=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[CH:16]2.C[N:27]([CH3:30])[CH:28]=O.C(Cl)Cl.[OH2:34]>C(OCC)(=O)C>[C:3]([O:4][CH:2]([CH2:30][NH:27][CH2:28][CH2:23][NH:22][C:14]1[C:13]([CH3:12])=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][NH:18]2)[CH2:1][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 31217Phenyl glycidyl etherHCID 202378485-Methyl-4-(2-aminoethylamino)-indazole

Product 1

HCID 538403351-Phenoxy-3-[2-(5-methylindazol-4-ylamino)-ethylamino]-propan-2-ol benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.0 g Phenyl glycidyl ether and 6.0 g 5-methyl-4-(2-aminoethylamino)-indazole are dissolved in 12 ml. dimethylformamide and left to stand for 2 days at ambient temperature. The reaction mixture is taken up in a little methylene chloride, shaken out three times with a 10-fold amount of water and the methylene chloride solution is dried and separated column chromatographically on silica gel using, as elution agent, methylene chloride-methanol-triethylamine (100:10:1 v/v/v). By evaporation of the pure fractions, there are obtained 5.2 g. of a dark oil, which is dissolved in a little ethyl acetate, mixed with 2.5 g. benzoic acid, filtered off with suction and recrystallized from ethyl acetate, with the use of active charcoal and fullers' earth. There are obtained 3.3 g. (36% of theory) of the desired product in the form of colorless crystals; m.p. 97°-103° C.

Workup

  1. dry with materialthe methylene chloride solution is dried
  2. customseparated column chromatographically on silica gel using
  3. washas elution agent, methylene chloride-methanol-triethylamine (100:10:1 v/v/v)
  4. customBy evaporation of the pure fractions, there
  5. customare obtained 5.2 g
  6. additionmixed with 2.5 g
  7. filtrationbenzoic acid, filtered off with suction
  8. customrecrystallized from ethyl acetate, with the use of active charcoal and fullers' earth
  9. customThere are obtained 3.3 g

Sources & evidence

ORD record
ord-6bf3dbf10aa94a418705d8dbee5508eb
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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