Water → HCID 21201854, compound

HRID 1979381Notes

Reaction equation

HRID 1979381 reaction equation
[C:1]1([CH3:38])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[NH:14][CH2:13][CH:12]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=3)=[O:24])[C:11]2=[O:37])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH2:39]([CH:41]([CH2:45][CH3:46])[C:42](Cl)=[O:43])[CH3:40].N1C=CC=CC=1.O>ClCCCl.C(OCC)(=O)C>[C:1]1([CH3:38])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:42](=[O:43])[CH:41]([CH2:45][CH3:46])[CH2:39][CH3:40])[CH2:13][CH:12]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:27]=3)=[O:24])[C:11]2=[O:37])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 759542-Ethylbutyryl chlorideHCID 212016301-[1-(2-toluoylmethyl)-2-oxo-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

Product 1

HCID 21201854HCID 21201854, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[1-(2-Toluoylmethyl)-2-oxo-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea (500 mg) obtained from Step 1 of Example 93 was suspended in 1,2-dichloroethane (10 ml), 2-ethyl-n-butanoyl chloride (144 mg) and pyridine (87 μl) were added thereto, the mixture was refluxed for 2 hours. Water (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture, and separated. The organic layer was washed with 1N hydrochloric acid, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 666 mg of the titled compound (Yield: 100%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customseparated
  3. washThe organic layer was washed with 1N hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-34f834d068ff4641922538ee4c798d4c
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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