Butyryl chloride → N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-butyramide

HRID 131352Notes

Reaction equation

HRID 131352 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3]1=[O:14].[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18]>>[O:9]=[C:8]1[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3](=[O:14])[CH:2]1[NH:1][C:15](=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 8855Butyryl chlorideHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58625910N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-butyramideYield 76.2%

Procedure

Using the method of Example 53, using 3-amino-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione (4.0 g, 20.9 mmol), butyryl chloride (2.45 g, 23.0 mmol) and overnight at RT gives the title compound (4.16 g, yield 76%); 1H NMR (300 MHz, DMSO-d6): δ 10.70 (s, 2H), 8.21 (d, 1H, J=7.8 Hz), 7.24-7.15 (m, 4H), 4.74 (d, 1H, J=7.5 Hz), 2.24 (t, 2H, J=7.2 Hz), 1.51-1.43 (m, 2H), 0.83 (t, 3H, J=7.5 Hz).

Workup

  1. customat RT

Sources & evidence

ORD record
ord-8ab7a04f05de4983aa4908427e48187c
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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