Riboflavin → Tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate

HRID 473704Notes

Reaction equation

HRID 473704 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([C:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=3)=[N:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>O1CCOCC1.[OH-].[Pd+2].[OH-].[Pd]>[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]3)=[N:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 493570RiboflavinHCID 59374116tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59374021Tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.87 g, 7.79 mmol) in 1,4-dioxane (39 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NEW (0.27 g, 0.39 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 1 day. The reaction was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and chromatographed via flash column chromatography (20% to 60% EtOAc/Hexanes) to provide tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate as a cream solid. MS (ESI, pos. ion) m/z: 393.0 [M+1+Na].

Workup

  1. filtrationThe reaction was filtered via a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed via flash column chromatography (20% to 60% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-51c4b724c469402ca8a2637a403b6cf9
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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