HCID 178418361, compound → HCID 178483559, compound

HRID 2274392Notes

Reaction equation

HRID 2274392 reaction equation
[F:1][C:2]1[C:3]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[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]>[CH3:31][N:29]([CH3:30])[CH2:28][CH2:27][CH2:26][O:25][C:3]1[C:2]([F:1])=[CH:24][C:6]2[N:7]=[C:8]([C:10]3[C:14]([NH2:15])=[CH:13][N:12]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][O:19]4)[N:11]=3)[NH:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178483560HCID 178483560, compound

Product 1

HCID 178483559HCID 178483559, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2.3 g of (3-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yloxy}propyl)dimethylamine in 40 mL of methanol and 0.2 g 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. 2.0 g of 3-[6-(3-dimethylaminopropoxy)-5-fluoro-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine are obtained in the form of a brown solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.46 to 2.21 (m, 8H); 2.17 (s, 6H); 2.40 (t, J=7.0 Hz, 2H); 3.63 (m, 1H); 3.95 (m, 1H); 4.08 (m, 2H); 4.92 (broad s, 2H); 5.32 (dd, J=2.5 and 10.0 Hz, 1H); from 7.01 to 7.47 (m, 2H); 7.31 (s, 1H); 12.55 (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-57f3b8a47a744f4bb8452d1e820cd1d8
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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