Allylamine → HCID 20040879, compound

HRID 1762437Notes

Reaction equation

HRID 1762437 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][NH:11][C:3]=12.[CH2:18]([NH2:21])[CH:19]=[CH2:20]>C1(C)C(C)=CC=CC=1>[CH2:18]([NH:21][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][NH:11][C:3]=12)[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 178426078HCID 178426078, compound

Product 1

HCID 20040879HCID 20040879, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 7-chloro-5-methyl-3-phenyl-1H-pyrazolo[4,3-b]pyridine (D9) (1 g), xylene (80 ml) and allylamine (20 ml) was placed in a Parr pressure vessel and heated at 142° rising to 162° for 2 days during which time the internal pressure rose to 75 psi. The vessel was then allowed to cool, the pressure released and the contents evaporated to dryness. The residue was chromotographed on basic alumina eluting with ether and then a rising percentage of methanol (to 25%). Approximately 90% of the starting material was recovered. The fractions containing the required product were combined, evaporated to dryness and recrystallised from ether/pentane with charcoal decolourisation to give the title compound as an off-white crystalline solid, m.p. 92°-105° followed by resolidification and melting 171°-177°.

Workup

  1. temperatureheated at 142°
  2. temperatureto cool
  3. customthe contents evaporated to dryness
  4. customApproximately 90% of the starting material was recovered
  5. additionThe fractions containing the required product
  6. customevaporated to dryness
  7. customrecrystallised from ether/pentane with charcoal decolourisation

Sources & evidence

ORD record
ord-53cd0552d0a04af19b766ffff3ef3577
Source dataset
uspto-grants-1989_05
Patent number
US04833136

Reaction notes

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