Water → Tert-butyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

HRID 473713Notes

Reaction equation

HRID 473713 reaction equation
F[C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[N:26][CH:27]=1.CC(C)([O-])C.[Na+].O>CS(C)=O>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:3]2[C:2]([O:35][C:32]3[CH:31]=[CH:30][C:29]([NH:28][C:25]4[CH:24]=[CH:23][C:22]([CH3:21])=[CH:27][N:26]=4)=[CH:34][CH:33]=3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 59351396Tert-butyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylateHCID 593739864-(5-Methylpyridin-2-ylamino)phenol

Product 1

HCID 59373921Tert-butyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of tert-butyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylate (9.55 mL, 3.73 mmol), 4-(5-methylpyridin-2-ylamino)phenol (0.747 g, 3.73 mmol), and sodium tert-butoxide (1.07 g, 11.20 mmol) in DMSO (15 mL) was stirred at RT in 24 h. Water was added, and the reaction mixture was extracted with ether (3×), dried over MgSO4, concentrated and purified by ISCO (0-60% EtOAc/Hexanes) to give the light brown oil. MS (ESI, pos. ion) m/z: 462.2 (M+1).

Workup

  1. extractionthe reaction mixture was extracted with ether (3×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by ISCO (0-60% EtOAc/Hexanes)
  5. customto give the light brown oil

Sources & evidence

ORD record
ord-fb54f3d6ab464d388278e2f5d350c3f5
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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