1,1'-Carbonyldiimidazole → HCID 9891640, compound

HRID 487608Notes

Reaction equation

HRID 487608 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:5].[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36]>O1CCCC1>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([CH2:27][C:25]2[CH:26]=[C:2]3[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]4[CH2:12][CH:13]=[C:14]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[CH2:15][CH2:16]4)[C:35](=[O:36])[NH:1]3)=[CH:23][CH:24]=2)[CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19092351HCID 19092351, compound

Product 1

HCID 9891640HCID 9891640, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-(4-methylpiperazin-1-ylmethyl)-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin 1-yl)butyl]benzamide (0.25 g), carbonyldiimidazole (0.45 g) and dry tetrahydrofuran (10 ml) was stirred under reflux for 14 hours. After evaporation of the solvent, the crude residue was taken up with ethyl acetate, washed with water, dried over magnesium sulfate and evaporated to give crystals. Recrystallization from ethanol afforded 7-(4-methylpiperazin-1-ylmethyl)-3-[4-(4-phenyl-1,2,3,6-tetrahydropyridin 1-yl)butyl]-1,2,3,4-tetrahydroquinazoline-2,4-dione (0.16 g).

Workup

  1. temperatureunder reflux for 14 hours
  2. customAfter evaporation of the solvent
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give crystals
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a9467b9d95724d919152be38a40bd109
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

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