Butylamine → Cartazolate

HRID 1576819Notes

Reaction equation

HRID 1576819 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 37015Cartazolate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 50.8 g. of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.2 mol.) in 200 ml. of benzene, 29.2 g. of n-butylamine (0.4 mol.) are added. The mixture is kept at 50° for 5 hours. Then the separated butylamine hydrochloride is filtered under suction and the filtrate is evaporated in vacuo to dryness. The residual 4-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester is recrystallized from hexane, m.p. 82°-83°, yield 53 g. (91.5%).

Workup

  1. filtrationThen the separated butylamine hydrochloride is filtered under suction
  2. customthe filtrate is evaporated in vacuo to dryness
  3. customThe residual 4-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester is recrystallized from hexane, m.p. 82°-83°, yield 53 g

Sources & evidence

ORD record
ord-8e5474ff211d43a4b4bd983d485b4a89
Source dataset
uspto-grants-1976_09
Patent number
US03983128

Reaction notes

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