Hydrazine → HCID 86732472, compound

HRID 1776444Notes

Reaction equation

HRID 1776444 reaction equation
[Cl:1][C:2]1[C:32]([N+:33]([O-])=O)=[CH:31][CH:30]=[C:29]([Cl:36])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1.NN>CO.[Ni]>[NH2:33][C:32]1[C:2]([Cl:1])=[C:3]([C:29]([Cl:36])=[CH:30][CH:31]=1)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 71554055HCID 71554055, compound

Product 1

HCID 86732472HCID 86732472, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

52 mg of 2-[1-(2,6-dichloro-3-nitrobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (2-44-1, 0.10 mmol, 1.0 eq.) were dissolved in 5.2 ml of dry methanol. 23.4 mg raney nickel (50%, 0.199 mmol, 2.0 eq.) and 0.045 ml hydrazine (35%, 0.498 mmol, 5.0 eq) were added. The reaction mixture was stirred at room temperature vigorously over night. The slurry was filtered over celite and washed with methanol twice. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography to yield 19.2 mg (0.04 mmol, 38%) of the analytically pure target compound.

Workup

  1. filtrationThe slurry was filtered over celite
  2. washwashed with methanol twice
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography
  5. customto yield 19.2 mg (0.04 mmol, 38%) of the analytically pure target compound

Sources & evidence

ORD record
ord-80e45ff387cc4ee2bbcd5e289fba411a
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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