N-Boc-hexahydro-1H-azepin-4-one → tert-Butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)azepane-1-carboxylate

HRID 474967Notes

Reaction equation

HRID 474967 reaction equation
O=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][NH2:24])[N:18]=1>CCOCC>[Br:16][C:17]1[N:18]=[C:19]([NH:23][N:24]=[C:2]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 193925882-Bromo-6-hydrazinopyridine

Product 1

HCID 76664798tert-Butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)azepane-1-carboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 4-oxoazepane-1-carboxylate (1.7 g, 8.1 mmol) was added to a solution of 2-bromo-6-hydrazinylpyridine (1.5 g, 8.1 mmol) in Et2O (27 mL), and the resulting solution was stirred at ambient temperature for 1.5 h. The solution was concentrated under reduced pressure to provide the title compound (3.1 g, 99%) as a light orange solid: 1H NMR (300 MHz, DMSO-d6) δ 9.89-9.68 (m, 1H), 7.50-7.45 (m, 1H), 7.04-7.01 (m, 1H), 6.89-6.85 (m, 1H), 3.48-3.28 (m, 4H), 2.59-2.50 (m, 4H, overlaps with H2O), 1.69-1.53 (m, 2H), 1.38-1.36 (m, 9H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ab4bfc0657143868712f6cb35d40986
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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