Hydrazine → HCID 58204625, compound

HRID 1498436Notes

Reaction equation

HRID 1498436 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-a897b576d1f14b729f38b65e328cfd92
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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