HCID 178418361, compound → HCID 178452211, compound

HRID 2274435Notes

Reaction equation

HRID 2274435 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:36]([F:37])=[CH:35][C:17]3[N:18]=[C:19]([C:21]4[C:25]([N+:26]([O-])=O)=[CH:24][N:23]([CH:29]5[CH2:34][CH2:33][CH2:32][CH2:31][O:30]5)[N:22]=4)[NH:20][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:36]([F:37])=[CH:35][C:17]3[N:18]=[C:19]([C:21]4[C:25]([NH2:26])=[CH:24][N:23]([CH:29]5[CH2:34][CH2:33][CH2:32][CH2:31][O:30]5)[N:22]=4)[NH:20][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178452212HCID 178452212, compound

Product 1

HCID 178452211HCID 178452211, compoundYield 177%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 540 mg of 4-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}piperazine-1-carboxylic acid tert-butyl ester in 15 mL of methanol and 54 mg of palladium-on-charcoal is hydrogenated under 1 bar of hydrogen pressure at ambient temperature for 16 hours. The reaction medium is filtered through celite and the filtrate is concentrated under reduced pressure in a rotary evaporator. 900 mg of 4-{2-[4-amino-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-fluoro-3H-benzimidazol-5-yl}piperazine-1-carboxylic acid tert-butyl ester are obtained in the form of a black solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.30 to 2.20 (m, 6H); 1.42 (s, 9H); 3.00 (m, 4H); 3.52 (m, 4H); 3.67 (m, 1H); 3.96 (m, 1H); 5.55 (broad d, J=10.0 Hz, 1H); 7.22 (d, J=7.5 Hz, 1H); 7.46 (d, J=12.5 Hz, 1H); 8.17 (s, 1H). ES mass spectrum: m/z=486 MH+ (base peak).

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-ebec2129b51a4458a850bc095a535185
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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