Tert-butyl 4-(2-chloro-4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)piperidine-1-carboxylate

HRID 454946Notes

Reaction equation

HRID 454946 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH2:10]2)[C:5]([C:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]=2)=[CH:4][N:3]=1>CO.[Pd]>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[N:11]1[CH2:12][CH:9]([O:8][C:6]2[C:5]([CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)=[CH:4][N:3]=[CH:2][N:7]=2)[CH2:10]1

Participants

4

Reactant 1

HCID 58547741Tert-butyl 4-(2-chloro-4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58547690Tert-butyl 4-(4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)piperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(2-chloro-4-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (472 mg, 0.95 mmol) in MeOH (10 mL) was added Pd/C (10%, 200 mg). The reaction solution was stirred at room temperature overnight under H2 atmosphere. The mixture was filtered through CELITE® and concentrated to give the product (307 mg, 0.66 mmol, yield: 78%). ESI-MS (M+1): 462 calc. for C26H31N5O3 461.

Workup

  1. filtrationThe mixture was filtered through CELITE®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-160e494d300b4823bb2a61f540fce122
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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