Acetic Anhydride → HCID 22405053, compound

HRID 441260Notes

Reaction equation

HRID 441260 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([CH2:12][N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24](=[O:47])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=4)=[CH:27][CH:26]=3)[CH2:16][CH2:15][C:14]2=[O:48])=[O:11])[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:56](OC(=O)C)(=[O:58])[CH3:57]>ClCCl.CN(C)C1C=CN=CC=1>[C:56]([O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([CH2:12][N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([C:24](=[O:47])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=4)=[CH:27][CH:26]=3)[CH2:16][CH2:15][C:14]2=[O:48])=[O:11])[CH2:6][CH2:5]1)(=[O:58])[CH3:57]

Participants

6

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 22405184HCID 22405184, compound

Product 1

HCID 22405053HCID 22405053, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl}-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (178 mg) and triethylamine (31 mg) in dichloromethane (4 ml) was added acetic anhydride (31 mg) and the mixture was stirred at ambient temperature for 1.5 hours. To the mixture was added 4-dimethylaminopyridine (10 mg) and acetic anhydride (10 mg), and then the mixture was stirred at ambient temperature for 15 minutes. The resulting mixture was diluted with dichloromethane and the organic layer was washed successively with saturated aqueous sodium bicarbonate solution and brine. Drying, filtering and the removal of solvents afforded a crude product. The crude product was triturated with a mixture of diethyl ether and n-hexane (1:1) to give 1-{[4-(2-acetoxyethyl)-1-piperazinyl]-carbonylmethyl)-5-{4-[2-(4-methylphenyl)benzoylamino]-benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (205 mg) as a slightly-yellow powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 15 minutes
  2. washthe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and brine
  3. customDrying
  4. filtrationfiltering
  5. customthe removal of solvents
  6. customafforded a crude product
  7. customThe crude product was triturated with a mixture of diethyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-6e2b772d283a436c8d123fd6f513395a
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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