Ethylamine → HCID 59198502, compound

HRID 2261196Notes

Reaction equation

HRID 2261196 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]=[CH:12][C:3]=12.[CH2:22]([NH2:24])[CH3:23]>>[CH2:22]([NH:24][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]=[CH:12][C:3]=12)[CH3:23]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 59198519HCID 59198519, compound

Product 1

HCID 59198502HCID 59198502, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-1-(4-methoxy-benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (350 mg, 1.16 mmol), ethyl amine (70 wt. % solution in water, 2 mL, 25 mmol) is heated at 120° C. in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 4 mL) and heated at 50° C. After stirring for 1.5 hours, the reaction mixture is basified with saturated sodium bicarbonate solution to pH=8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a solid. MS m/z 311.2 (M+1).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in HCl solution (1N, 4 mL)
  4. temperatureheated at 50° C
  5. filtrationThe solid is collected by filtration
  6. washwashed with water
  7. dry with materialhexanes, dried

Sources & evidence

ORD record
ord-6073ef72c2bd4b00833e0929e155e05e
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

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