(R)-3-Pyrrolidinol → (R)-1-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)pyrrolidin-3-ol

HRID 1775586Notes

Reaction equation

HRID 1775586 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[Cl:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][N:11]=[C:10]2[N:20]([CH2:29][CH2:30]I)[N:21]=[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]=12>C(Cl)Cl>[Cl:7][C:8]1[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:12][N:11]=[C:10]2[N:20]([CH2:29][CH2:30][N:1]3[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]3)[N:21]=[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:9]=12

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 866970204-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 66576255(R)-1-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)pyrrolidin-3-olYield 16.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-3-pyrrolidinol (166 mg, 1.9 mmol) in CH2Cl2 (1.5 ml) was added to 4-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (example 74 step 1) (113 mg, 0.24 mmol) and the reaction stirred at ambient for 24 h. The resultant residue was purified using chromatography (silica gel, gradient 20 to 100% ethyl acetate/isohexane, then 0 to 100% ethyl acetate/acetone) followed by preparative HPLC to give Compound 83 as an orange solid (17 mg).

Workup

  1. customThe resultant residue was purified

Sources & evidence

ORD record
ord-fbd89dddcae546579c8a47af85943788
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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