Pyrrolidine → 2-(4-chloro-3-(3-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-1-(pyrrolidin-1-yl)ethanone

HRID 1775583Notes

Reaction equation

HRID 1775583 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]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31]O[CH2:29][CH2:28]3)=[O:26])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=3)[C:3]=12.[F:33]C1C=C(C=CC=1)C(CC#N)=O.N1CCCC1>>[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]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][CH2:29][CH2:28]3)=[O:26])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:33])[CH:18]=3)[C:3]=12

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 27589483-(3-Fluorophenyl)-3-oxopropanenitrileHCID 665761742-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-1-morpholinoethanone

Product 1

HCID 665761782-(4-chloro-3-(3-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)-1-(pyrrolidin-1-yl)ethanone

Procedure

Example 72 (Compound 79) was synthesised following a similar procedure outlined in Example 68 (Compound 75), using 3-fluorobenzoylacetonitrile instead of 4-fluorobenzoylacetonitrile in step 1 and pyrrolidine instead of morpholine in step 7. Compound 79 was obtained as a yellow solid (13.1 mg).

Workup

  1. customExample 72 (Compound 79) was synthesised

Sources & evidence

ORD record
ord-18045550ca474a8799f300f3368fcc95
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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