Hydrazine → HCID 59168049, compound

HRID 1443805Notes

Reaction equation

HRID 1443805 reaction equation
[N+:1]([C:4]1[C:5]([NH:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[N:8][CH:9]=1)([O-])=O.NN>CO.[Ni]>[NH2:1][C:4]1[C:5]([NH:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 59168047HCID 59168047, compound

Product 1

HCID 59168049HCID 59168049, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of N-{2-[(5-nitro-2-{[(3,4-dichlorophenyl)methyl]amino}pyrimidin-4-yl)amino]ethyl}(tert-butoxy)carboxamide, prepared as described in Example 4, (1.5 g, 3.28 mmol) in MeOH (100 mL) was added hydrazine (1.8 mL of 65% v/v aq. solution, 33 mmol). The reaction mixture was heated to 60° C. Raney Ni was added in portions to keep evolution of nitrogen steady. After 1 h the reaction mixture was cooled to room temperature, catalyst filtered off, and the filter cake washed with MeOH. The resulting solution was concentrated and purified by chromatography eluting with MeOH/dichloromethane gradient to provide compound N-{2-[(5-amino-2-{[(3,4-dichlorophenyl)methyl]amino}pyrimidin-4-yl)amino]ethyl}(tert-butoxy)carboxamide as tan solid. Compound was used in the next step without purification.

Workup

  1. customprepared
  2. temperatureAfter 1 h the reaction mixture was cooled to room temperature
  3. filtrationcatalyst filtered off
  4. washthe filter cake washed with MeOH
  5. concentrationThe resulting solution was concentrated
  6. custompurified by chromatography
  7. washeluting with MeOH/dichloromethane gradient

Sources & evidence

ORD record
ord-7be8ae436fa04dfc89e84b32afa8c353
Source dataset
uspto-grants-2010_02
Patent number
US07662819B2

Reaction notes

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