Potassium Hydroxide → HCID 19081249, compound

HRID 963518Notes

Reaction equation

HRID 963518 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11](=[O:30])[CH:10]([NH:31][C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=2)=[O:33])[N:9]=1.[OH-].[K+]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[C:11](=[O:30])[CH:10]([NH:31][C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=2)=[O:33])[N:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19081162HCID 19081162, compound

Product 1

HCID 19081249HCID 19081249, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methoxycarbonylpyridin-2-yl)methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.35 g) in 1,4-dioxane (13 ml) was added an aqueous solution of potassium hydroxide (0.35 g in 5 ml of water) at room temperature and the mixture was stirred overnight at ambient temperature. The resultant mixture was concentrated in vacuo and the residue was taken up with 10 ml water and washed with isopropyl ether. The aqueous layer was adjusted to pH 7.0 with 10% citric acid aqueous solution and extracted with chloroform. The organic layer was dried over sodium sulfate, filtered and concentrarted in vacuo. The crude compound was purified by column chromatography on silica gel with a mixture of chloroform and methanol to give N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-hydroxycarbonyl-pyridin-2-yl)methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea as a yellow form, which was triturated by isopropyl ether and collected by suction (0.08 g).

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. washwashed with isopropyl ether
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe crude compound was purified by column chromatography on silica gel with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-991c09dbe5ab487496d35f3093b1851e
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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