1,2-Ethanediamine, N1,N1,N2-trimethyl- → 4-chloro-3,5-diphenyl-1-vinyl-1H-pyrazolo[3,4-c]pyridazine

HRID 1775585Notes

Reaction equation

HRID 1775585 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:23][CH2:24]I)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.CNCCN(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[C:4]2[N:14]([CH:23]=[CH2:24])[N:15]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:3]=12

Participants

4

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 866970204-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665762544-chloro-3,5-diphenyl-1-vinyl-1H-pyrazolo[3,4-c]pyridazineYield 32.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (53 mg, 0.11 mmol) in CH2Cl2 (1.5 ml) was added to trimethylethylene diamine (97 mg, 0.95 mmol) and the mixture stirred at ambient temperature for 3 days. The solvent was removed in vacuo and the crude purified by chromatography (silica gel, gradient 5 to 100% ethyl acetate/isohexane) to give Compound 82 as a yellow solid (12 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude purified by chromatography (silica gel, gradient 5 to 100% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-85cb0814fa95427b912d1bacde1dcf8d
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

Loading…