Potassium Carbonate → 2-(6-{4-[(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-1-oxo-4a,5,8,8a-tetrahydro-1H-phthalazin-2-yl]-piperidin-1-yl}-hexyl)-isoindole-1,3-dione

HRID 585488Notes

Reaction equation

HRID 585488 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[C@@H:38]3[C@@H:33]([CH2:34][CH:35]=[CH:36][CH2:37]3)[C:32](=[O:39])[N:31]([CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]2[C@@H:38]3[C@@H:33]([CH2:34][CH:35]=[CH:36][CH2:37]3)[C:32](=[O:39])[N:31]([CH:40]3[CH2:45][CH2:44][N:43]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]4[C:16](=[O:17])[C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:9]4=[O:18])[CH2:42][CH2:41]3)[N:30]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 141120N-(6-Bromohexyl)phthalimideHCID 68878852(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-2-piperidin-4-yl-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one

Product 1

HCID 697947122-(6-{4-[(4aS,8aR)-4-(3,4-Dimethoxy-phenyl)-1-oxo-4a,5,8,8a-tetrahydro-1H-phthalazin-2-yl]-piperidin-1-yl}-hexyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 mmol of 2-(6-bromo-hexyl)-isoindole-1,3-dione, 6 mmol of compound 5c and 3 g of potassium carbonate in 50 ml of dimethylformamide is stirred for 18 h at RT. After evaporating the solvent, the residue is partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated. The residue is purified by chromatography (ethyl acetate:hexane/4:1). M. p. 39-44° C.

Workup

  1. customAfter evaporating the solvent
  2. customthe residue is partitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified by chromatography (ethyl acetate:hexane/4:1)

Sources & evidence

ORD record
ord-c666d165ed1d48ce93fa309741bffbcd
Source dataset
uspto-grants-2005_08
Patent number
US06933296B2

Reaction notes

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