HCID 178418361, compound → HCID 178483735, compound

HRID 2274419Notes

Reaction equation

HRID 2274419 reaction equation
[F:1][C:2]1[C:3]([NH:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[CH:4][C:5]2[NH:9][C:8]([C:10]3[C:14]([N+:15]([O-])=O)=[CH:13][N:12]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[N:11]=3)=[N:7][C:6]=2[CH:24]=1.[H][H]>CO.[Pd]>[NH2:15][C:14]1[C:10]([C:8]2[NH:9][C:5]3[CH:4]=[C:3]([NH:25][CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[C:2]([F:1])=[CH:24][C:6]=3[N:7]=2)=[N:11][N:12]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:13]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178483736HCID 178483736, compound

Product 1

HCID 178483735HCID 178483735, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

350 mg of N1-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}-N2,N2-dimethylethane-1,2-diamine in 15 mL of methanol and 40 mg of palladium-on-charcoal are hydrogenated under 1 bar of hydrogen pressure at 22° C. for 16 hours. The reaction medium is filtered through celite and the filtrate is concentrated under reduced pressure in a rotary evaporator. 300 mg of N1-{2-[4-amino-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-fluoro-3H-benzimidazol-5-yl}-N2,N2-dimethylethane-1,2-diamine are obtained. The compound is used as it is for the subsequent stage.

Workup

  1. filtrationThe reaction medium is filtered through celite
  2. concentrationthe filtrate is concentrated under reduced pressure in a rotary evaporator

Sources & evidence

ORD record
ord-9c77cfa8c52149ea9251c90272e273f9
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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