Ethanolamine → HCID 20040893, compound

HRID 1762440Notes

Reaction equation

HRID 1762440 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][NH:15][C:7]=12>C1(C)C(C)=CC=CC=1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:8]3=[N:9][C:10]([CH3:12])=[CH:11][C:6]([NH:4][CH2:3][CH2:1][OH:2])=[C:7]3[NH:15][N:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178426079HCID 178426079, compound

Product 1

HCID 20040893HCID 20040893, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of ethanolamine (5 ml) and 7-chloro-5-methyl-3-(4-chlorophenyl)-1H-pyrazolo[4,3-b]pyridine (D16) (0.6 g) were heated under reflux in xylene (10 ml) under nitrogen for 48 h. The mixture was evaporated to dryness in vacuo and dissolved in a mixture of water (40 ml) and methanol (60 ml). The pH of the solution was adjusted to ca. 12 with 10% sodium hydroxide solution and then the solution was evaporated to one third volume in vacuo. The resulting precipitate (0.6 g) was collected, washed with water, and recrystallised from ethyl acetate-methanol (trace) to afford the title compound (0.42 g), m.p. 222°-224° C.

Workup

  1. temperaturewere heated
  2. customThe mixture was evaporated to dryness in vacuo
  3. dissolutiondissolved in a mixture of water (40 ml) and methanol (60 ml)
  4. customthe solution was evaporated to one third volume in vacuo
  5. customThe resulting precipitate (0.6 g) was collected
  6. washwashed with water
  7. customrecrystallised from ethyl acetate-methanol (trace)

Sources & evidence

ORD record
ord-6a951e1aa56646aab8a022a7eedcd112
Source dataset
uspto-grants-1989_05
Patent number
US04833136

Reaction notes

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