Water → HCID 86620086, compound

HRID 969488Notes

Reaction equation

HRID 969488 reaction equation
[CH3:1][C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[C:9]([C:22]([OH:24])=O)[C:10]3[CH2:11][CH2:12][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:14][C:15]=3[C:4]=2[N:3]=1.[NH:25]1[CH2:27][CH2:26]1.O>O1CCCC1>[N:25]1([C:22]([C:9]2[C:10]3[CH2:11][CH2:12][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:14][C:15]=3[C:4]3[N:3]=[C:2]([CH3:1])[N:6]([CH3:7])[C:5]=3[CH:8]=2)=[O:24])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 9033AziridineHCID 69134413HCID 69134413, compound

Product 1

HCID 86620086HCID 86620086, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 260 mg (0.81 mmol) 2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]-imidazole-5-carboxylic acid in tetrahydrofuran (10 ml) were added 157 mg (1.0 mmol) N,N′-carbonyl-diimidazole (CDI) and the reaction was stirred at room temperature overnight 105 mg (2.4 mmol) Aziridine were added and the mixture was stirred for 16 h at room temperature. The reaction was poured into water and extracted with dichloromethane. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=20:1) and crystallized from n-butanol to afford 56 mg (20%) of the title compound as a white solid. m.p. 201°-204° C.

Workup

  1. additionwere added
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane/methanol=20:1)
  6. customcrystallized from n-butanol

Sources & evidence

ORD record
ord-7f21f0325cd0489d9548474db0383807
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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