HCID 136168706, compound → HCID 136168685, compound

HRID 2274430Notes

Reaction equation

HRID 2274430 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([C:16]4[C:20]([N+:21]([O-])=O)=[CH:19][N:18]([CH:24]5[CH2:29][CH2:28][CH2:27][CH2:26][O:25]5)[N:17]=4)[NH:13][C:12]=3[CH:30]=2)[CH2:4][CH2:3]1.[H][H]>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([C:16]4[C:20]([NH2:21])=[CH:19][N:18]([CH:24]5[CH2:29][CH2:28][CH2:27][CH2:26][O:25]5)[N:17]=4)[NH:13][C:12]=3[CH:30]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 136168706HCID 136168706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136168685HCID 136168685, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 370 mg of 6-(4-methylpiperazin-1-yl)-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzimidazole in 10 mL of methanol and 37 mg of palladium-on-charcoal is hydrogenated under 1 bar of hydrogen pressure at ambient temperature for 18 hours. The reaction medium is filtered through celite and the filtrate is concentrated under reduced pressure in a rotary evaporator. 360 mg of 3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine are obtained in the form of a black oil. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.50 to 2.21 (m, 6H); 2.23 (s, 3H); 2.50 (m masked, 4H); 3.08 (m, 4H); 3.61 (m, 1H); 3.94 (m, 1H); from 4.89 to 4.98 (m, 2H); 5.30 (broad d, J=10.0 Hz, 1H); from 6.85 to 7.12 (m, 2H); from 7.25 to 7.46 (m, 2H); from 12.2 to 12.35 (m, 1H).

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-f615f2915e90475191607eee49b02e2a
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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