Butylamine → Cartazolate

HRID 1658752Notes

Reaction equation

HRID 1658752 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 5.08 g of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.02 mol) in 20 ml of benzene is added 2.92 g of n-butylamine (0.04 mol). This mixture is kept at room temperature for 3 days. After this time, the separated butylamine hydrochloride is filtered under suction and the filtrate is evaporated in vacuo to dryness. The residue, 4-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethylester, is recrystallized from hexane, m.p. 82°-83°. The total yield amounts to 5.3 g = 91.5% of theory.

Workup

  1. filtrationAfter this time, the separated butylamine hydrochloride is filtered under suction
  2. customthe filtrate is evaporated in vacuo to dryness
  3. customThe residue, 4-butylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethylester, is recrystallized from hexane, m.p. 82°-83°
  4. customThe total yield

Sources & evidence

ORD record
ord-fd11d90144dc4c388339ef5ecd2bd124
Source dataset
uspto-grants-1976_06
Patent number
US03966746

Reaction notes

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