Hydrazine → HCID 58204625, compound

HRID 2044595Notes

Reaction equation

HRID 2044595 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22]([C:28]([O:30]CC)=O)[C:23]([O:25]CC)=O)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:33]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[NH2:34][NH2:35]>C(O)C>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([CH:22]5[C:28](=[O:30])[NH:35][NH:34][C:23]5=[O:25])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:33]=2)=[N:7][CH:6]=[N:5]1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67050763HCID 67050763, compound

Product 1

HCID 58204625HCID 58204625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 181 mg (0.40 mmol) of diethyl 2-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)malonate and 0.314 mL (10.0 mmol) of hydrazine in 4.0 ml of Ethanol was heated at 75° C. for 18 hours. The mixture was concentrated, the residue triturated with acetic acid. A precipitate was filtered off, washed with acetic acid, ethyl ether and recrystallized from ethyl ether/ethanol mixture to give 360. Yield 59 mg (37.5%). M/z 394.1, calc. 393.15. 1H NMR (400 MHz, DMSO) δ 10.20 (s, 2H), 8.29 (d, J=8.6, 1H), 7.89 (d, J=12.9, 2H), 7.70 (d, J=8.5, 1H), 7.63 (s, 1H), 5.93 (dt, J=13.1, 6.7, 1H), 4.48 (d, J=7.2, 4H), 1.49 (d, J=6.6, 6H)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with acetic acid
  3. filtrationA precipitate was filtered off
  4. washwashed with acetic acid, ethyl ether
  5. customrecrystallized from ethyl ether/ethanol mixture

Sources & evidence

ORD record
ord-fbdece14054c4c868c0deb09f1aeee43
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

Loading…