HCID 58014521, compound → HCID 58014461, compound

HRID 1876869Notes

Reaction equation

HRID 1876869 reaction equation
[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=4)[N:16]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:17]2[N:16]=[C:15]([C:13]3[CH:12]=[N:11][N:10]([CH:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][C:8]#[N:9])[CH:14]=3)[CH:20]=[CH:19][N:18]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 58014521HCID 58014521, compound

Product 1

HCID 58014461HCID 58014461, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-cyclopentyl-3-(4-(2-(4-nitrophenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile (1.00 g, 0.00248 mol) in 20 mL of methanol was hydrogenated in the presence of catalytic amount of 10% Pd/C, under balloon pressure, overnight. The catalyst was filtered off and the filtrate was evaporated to dryness. The crude product was used directly in next step (900 mg, 97.2%). An analytically pure sample was obtained by RP-HPLC as a racemic mixture. LCMS (M+H) 374.4.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customAn analytically pure sample was obtained by RP-HPLC as a racemic mixture

Sources & evidence

ORD record
ord-731bcba749004b24bf52d6d8e34a8c94
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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