Water → HCID 15751520, compound

HRID 1974630Notes

Reaction equation

HRID 1974630 reaction equation
[CH2:1]([O:8][NH:9][C:10]([CH2:12][C:13]1[N:17]([CH:18]2[CH2:20][CH2:19]2)[C:16]2[CH:21]=[C:22]([N:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[C:23]([F:25])=[CH:24][C:15]=2[N:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.O.[O:51]1CCC[CH2:52]1>>[CH2:1]([O:8][N:9]1[C:10](=[O:11])[CH:12]=[C:13]2[N:17]([CH:18]3[CH2:19][CH2:20]3)[C:16]3[CH:21]=[C:22]([N:26]4[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]4)[C:23]([F:25])=[CH:24][C:15]=3[N:14]2[C:52]1=[O:51])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15751504HCID 15751504, compound

Product 1

HCID 15751520HCID 15751520, compoundYield 5%

Procedure

tert-Butyl 4-[2-[[(benzyloxy)carbamoyl]methyl]-1-cyclopropyl-5-fluoro-6-benzimidazolyl]-1-piperazinecarboxylate (779 mg, 1.18 mmol) is dissolved in tetrahydrofuran (15 ml) and treated with N,N'-carbonyldiimidazole (480 mg, 2.96 mmol) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (225 mg, 1.48 mmol). The suspension obtained is poured into water (200 ml) and then extracted with ethyl acetate. The organic phase is washed in succession with water and 10 percent sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated under reduced pressure and the residue is chromatographed on silica gel (eluent: ethyl acetate/n-hexane 8:2). The product is crystallized from ethyl acetate/n-hexane. There are obtained 42 mg (5%) of tert-butyl 4-[2-(benzyloxy)-5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate.

Workup

  1. customThe suspension obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed in succession with water and 10 percent sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customthe residue is chromatographed on silica gel (eluent: ethyl acetate/n-hexane 8:2)
  7. customThe product is crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-6f57e5d60745463ea170b61a6164996b
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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