2-Butanol, 4-amino- → HCID 13059312, compound

HRID 1902609Notes

Reaction equation

HRID 1902609 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:9]2=[N:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[OH:19][CH:20]([CH3:24])[CH2:21][CH2:22][NH2:23]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:23][CH2:22][CH2:21][CH:20]([OH:19])[CH3:24])=[C:8]2[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:9]2=[N:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1702542-Butanol, 4-amino-HCID 13059311Ethyl 4-chloro-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 13059312HCID 13059312, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

2.75 each of 4-chloro-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester and 3-hydroxy-n-butylamine are combined with 15.6 ml of dry toluene under N2 and heated at 45° C. for 48 hours. The mixture was cooled to room temperature and the toluene layer was decanted from the oil that separated out. The toluene layer was washed with water and then dried and concentrated in vacuo to yield 3.7 g of product which crystallized on trituration with hexane. This was recrytallized from hexane to yield 1.91 g of white product mp 94.5°-96.5° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe toluene layer was decanted from the oil that
  3. customseparated out
  4. washThe toluene layer was washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ef737f1163e4242884b69fa4a3880b3
Source dataset
uspto-grants-1982_12
Patent number
US04364948

Reaction notes

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