Hydrazine → 3-((1S)-1-{1-[(S)-(4-chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzohydrazide

HRID 602989Notes

Reaction equation

HRID 602989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[N:9]2[CH2:12][CH:11]([CH:13]([C:18]3[CH:19]=[C:20]([CH:26]=[C:27]([F:29])[CH:28]=3)[C:21]([O:23]CC)=O)[C:14]([F:17])([CH3:16])[CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.[NH2:38][NH2:39]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[N:9]2[CH2:10][CH:11]([C@@H:13]([C:18]3[CH:19]=[C:20]([CH:26]=[C:27]([F:29])[CH:28]=3)[C:21]([NH:38][NH2:39])=[O:23])[C:14]([F:17])([CH3:16])[CH3:15])[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67055325HCID 67055325, compound

Product 1

HCID 670553323-((1S)-1-{1-[(S)-(4-chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 523 mg (0.41 mmol) of ethyl 3-(1-{l-[(4-chlorophenyl)(3-cyanophenyl)methyl] azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzoate (Preparation 17), 0.6 mL(1 6.36 mmol) of hydrazine, and 4 mL of EtOH was heated to reflux. After 8 h, the mixture was concentrated to remove solvents to afford the of title compound as an white solid. 1H-NMR(CDCl3) δ 1.20(d, 3H, J=21 Hz), 1.29(d, 3H, J=21 Hz), 2.32 (t, 3H, J=7.1 Hz), 2.85 (t, 1H, J=8 Hz), 2.94 (m, 1H), 3.06 (m, 1H), 3.20 (m, 1H), 3.51 (s, 2H), 3.63 (t, 1H, J=5 Hz), 4.26 (s, 1H), 7.06-7.71 (m, 11H); Mass Spectrum: m/e=509 (M+1, 35Cl), 511 (M+1, 37Cl).

Workup

  1. temperaturewas heated to reflux
  2. concentrationthe mixture was concentrated
  3. customto remove solvents

Sources & evidence

ORD record
ord-3e5f777cb90049faaf88ea490014652e
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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