1,1-Dimethylhydrazine → HCID 66685153, compound

HRID 1500614Notes

Reaction equation

HRID 1500614 reaction equation
C(O[C:4]([C:6]1[CH2:7][N:8]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:9][CH2:10][C:11]=1[NH:12][C:13]([O:15]C1C=CC=CC=1)=O)=[O:5])C.[CH3:31][N:32]([CH3:34])[NH2:33].C1CCN2C(=NCCC2)CC1.[OH-].[Na+]>C1COCC1.C(O)(=O)C>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([N:8]2[CH2:9][CH2:10][C:11]3[NH:12][C:13](=[O:15])[N:33]([N:32]([CH3:34])[CH3:31])[C:4](=[O:5])[C:6]=3[CH2:7]2)=[O:30])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66688781HCID 66688781, compound

Product 1

HCID 66685153HCID 66685153, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-4-phenoxycarbonylamino-1-(4-chlorobenzoyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (200 mg) was dissolved in THF (2 ml), N,N-dimethylhydrazine (142 μl) and DBU (10 μl) were added and the resultant mixture was shaken at 50° C. for 3 hours. 5 N sodium hydroxide solution (200 μl) was added and the resultant mixture was further shaken at 50° C. overnight. To the reaction solution, acetic acid (300 μl) was added to neutralize, and the reaction solution was then concentrated. The resultant residue was subjected to medium-pressure column fractionation (solvent; methanol:methylene chloride=0:100 to 7:93). The titled compound (105 mg) was obtained as a white powder.

Workup

  1. concentrationthe reaction solution was then concentrated

Sources & evidence

ORD record
ord-01bfa63c08fc4cfa943853c5f7dcc1c6
Source dataset
uspto-grants-2015_12
Patent number
US09206173B2

Reaction notes

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