Methylhydrazine → HCID 10297158, compound

HRID 1270190Notes

Reaction equation

HRID 1270190 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:32])[C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[CH3:35][NH:36][NH2:37]>C(O)C>[CH:26]1([C:23]2[CH:22]=[CH:21][C:20]([C:19]([N:10]3[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13][N:14]4[C:5]([C:3]([N:36]([CH3:35])[NH2:37])=[O:4])=[CH:6][CH:7]=[C:8]4[CH2:9]3)=[O:32])=[CH:25][CH:24]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 18449079HCID 18449079, compound

Product 1

HCID 10297158HCID 10297158, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,2,2-trichloro-1-[(10-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-1-ethanone of Example 7 (2.32 g) in absolute ethanol (50 mL) was treated with methylhydrazine (0.626 g). The mixture was refluxed for four hours and then all volatiles were removed in vacuo. The residue was treated with water and extracted with dichloromethane. The extracts were filtered through a short column of Magnesol®. The eluate was evaporated to dryness to provide the title compound as an amorphous yellow solid (0.18 g).

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. customall volatiles were removed in vacuo
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. filtrationThe extracts were filtered through a short column of Magnesol®
  6. customThe eluate was evaporated to dryness

Sources & evidence

ORD record
ord-f41fa0ec7c9a46d0bcb1addb3067736a
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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