Phthalimide → HCID 69308730, compound

HRID 2250624Notes

Reaction equation

HRID 2250624 reaction equation
[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([CH2:28]O)[C:10]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[C:6]2=[CH:5][CH:4]=1)[CH3:2].[C:30]1(=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[NH:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[O:40]=[C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[N:31]1[CH2:28][C:9]1[C:10]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)[C:6]2[N:7]([C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 68803924HCID 68803924, compound

Product 1

HCID 69308730HCID 69308730, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-[7-ethyl-2-(hydroxymethyl)-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate (100 mg), 1H-isoindole-1,3(2H) dione (44.6 mg) diisopropyl azodicarboxylate (76.7 mg) and triphenylphosphine (99.5 mg) in tetrahydrofuran (2 mL) was stirred at ambient temperature for 1 hour. After evaporation of solvent, the residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1-1:1) to give ethyl 5-[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-7-ethyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate as yellow oil (107 mg).

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with a mixture of hexane and ethyl acetate (20:1-1:1)

Sources & evidence

ORD record
ord-7c45fc87fb224e9c9162060b70152d50
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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