1,1'-Carbonyldiimidazole → HCID 15751512, compound

HRID 1974626Notes

Reaction equation

HRID 1974626 reaction equation
[C:1]([CH2:4][C:5]1[N:9]([CH:10]2[CH2:12][CH2:11]2)[C:8]2[CH:13]=[C:14]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[C:15]([F:17])=[CH:16][C:7]=2[N:6]=1)(=[O:3])[NH2:2].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32].N12CCCN=C1CCCCC2>C1COCC1>[CH:10]1([N:9]2[C:8]3[CH:13]=[C:14]([N:18]4[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]4)[C:15]([F:17])=[CH:16][C:7]=3[N:6]3[C:31](=[O:32])[NH:2][C:1](=[O:3])[CH:4]=[C:5]23)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15751500HCID 15751500, compound

Product 1

HCID 15751512HCID 15751512, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-[2-(carbamoylmethyl)-1-cyclopropyl-5-fluoro-6-benzimidazolyl]-1-piperazinecarboxylate (980 mg, 2.53 mmol) is suspended in THF (15 ml) and treated with 1,1'-carbonyldiimidazole (760 mg, 2 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 ml). The reaction mixture is heated to 60° for 2 hours, whereby white crystals separate. The suspension is then cooled to 0°. The crystals are filtered off and recrystallized from ethanol. There are obtained 760 mg (73%) of tert-butyl 4-[5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-1,3-dioxopyrimido-[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate.

Workup

  1. temperatureThe reaction mixture is heated to 60° for 2 hours
  2. customwhereby white crystals separate
  3. temperatureThe suspension is then cooled to 0°
  4. filtrationThe crystals are filtered off
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a709e5481ab5443c9c8b88723c8445bb
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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