1,1'-Carbonyldiimidazole → HCID 178518660, compound

HRID 2088375Notes

Reaction equation

HRID 2088375 reaction equation
[N:1]1([CH2:7][C:8]2[CH:22]=[CH:21][C:11]3[NH:12][C:13]([C:15]4[C:19]([NH2:20])=[CH:18][NH:17][N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:11](=[CH:21][CH:22]=2)[N:12]=[C:13]2[N:14]3[C:23](=[O:24])[NH:20][C:19]3[C:15]2=[N:16][NH:17][CH:18]=3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178508054HCID 178508054, compound

Product 1

HCID 178518660HCID 178518660, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine (3.2 g, 10.7 mmol) in anhydrous THF (50 mL) stirring at ambient temperature was added 1,1′-carbonyldiimidazole (1.78 g, 11 mmol). The mixture was heated at reflux for 14 h and then cooled to ambient. The solid formed was collected by filtration, washed with THF (20 mL) and dried in vacuo to give 7-morpholin-4-ylmethyl-2,4-dihydro-1,2,4,5a,10-pentaaza-cyclopenta[a]fluoren-5-one (2.34 g, 67% ) as a pink solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 h
  3. temperaturecooled
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. washwashed with THF (20 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d92139d7b2da4ad4845b075ffcdc975d
Source dataset
uspto-grants-2013_05
Patent number
US08435970B2

Reaction notes

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