1,1'-Carbonyldiimidazole → HCID 136104427, compound

HRID 1717419Notes

Reaction equation

HRID 1717419 reaction equation
[NH2:1]/[C:2](=[N:28]\[OH:29])/[CH2:3][CH2:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)[N:9]=[N:8][C:7]=1[C:22]([NH:24][CH:25]1[CH2:27][CH2:26]1)=[O:23].[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH:25]1([NH:24][C:22]([C:7]2[N:8]=[N:9][N:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:16]=3)[C:6]=2[CH2:5][CH2:4][CH2:3][C:2]2[NH:1][C:30](=[O:31])[O:29][N:28]=2)=[O:23])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 576650325-[(4Z)-4-amino-4-hydroxyiminobutyl]-N-cyclopropyl-1-[4-(ethylcarbamoyl)phenyl]triazole-4-carboxamide

Product 1

HCID 136104427HCID 136104427, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-[(4Z)-4-amino-4-(hydroxyimino)butyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (240 mg, 0.6 mmol) obtained in Example 1209 and 1,1′-carbonyldiimidazole (97 mg, 0.6 mmol) in THF (5 ml) was added DBU (91 mg, 0.6 mmol) at room temperature and the mixture was stirred at 50° C. for 3 hr and concentrated. The residue was dissolved in water (10 ml), adjusted to pH 4-5 with 1N hydrochloric acid and liberated oil was extracted with ethyl acetate (30 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1) to give the title compound as a colorless powder (150 mg, 59%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water (10 ml)
  3. extractionwas extracted with ethyl acetate (30 ml×2)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-b7414dbccc4a474680994d46acbbdedb
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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