Acetic Anhydride → 2-(4-acetyl-1-neopentyl-2-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl)-N-(2-fluorobenzyl)acetamide

HRID 1863988Notes

Reaction equation

HRID 1863988 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][NH:5][C:6](=[O:33])[CH2:7][CH:8]1[N:14]([C:15](=[O:22])[C:16]2C=CN=CC=2)[CH2:13][C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:9]1=[O:32].C(OC(=O)C)(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:15]([N:14]1[CH2:13][C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]([CH2:27][C:28]([CH3:30])([CH3:31])[CH3:29])[C:9](=[O:32])[CH:8]1[CH2:7][C:6]([NH:5][CH2:4][C:3]1[CH:34]=[CH:35][CH:36]=[CH:37][C:2]=1[F:1])=[O:33])(=[O:22])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 23089896N-(2-fluorobenzyl)-2-(4-isonicotinoyl-1-neopentyl-2-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl)acetamide

Product 1

HCID 230898722-(4-acetyl-1-neopentyl-2-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl)-N-(2-fluorobenzyl)acetamideYield 83.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of the compound (0.15 g) obtained in Example 1B (1) in pyridine (6 ml) were added acetic anhydride (0.20 g) and 4-dimethylaminopyridine (0.05 g), and the mixture was stirred at room temperature for 14 hrs. The solvent was evaporated, and the residue was purified by silica gel column chromatography and recrystallized from hexane-ethyl acetate to give the title compound (0.11 g) as colorless crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f0aa0d5178d54c5c96e214beb44dec88
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Reaction notes

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