Triethylamine → Cyclopentanecarboxylic acid (2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-amide

HRID 131357Notes

Reaction equation

HRID 131357 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].[CH:15]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>>[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:20]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:21]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58860677Cyclopentanecarboxylic acid (2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-amideYield 87%

Procedure

Using the method of Example 53, using 3-amino-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione (7.0 g, 36.6 mmol), cyclopentanecarbonyl chloride (5.34 g, 40.3 mmol) and triethyl amine (4.07 g, 40.3 mmol), overnight at RT giving the title compound (9.13 g, yield 87%). 1H NMR (300 MHz, DMSO-d6): δ 10.70 (s, 2H), 8.11 (d, 1H, J=7.8 Hz), 7.24-7.15 (m, 4H), 4.73 (d, 1H, J=7.5 Hz), 2.96-2.87 (m, 1H), 1.74-1.45 (m, 8H).

Workup

  1. customat RT

Sources & evidence

ORD record
ord-671701368d794ba48ac6fb8b59f09f62
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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