HCID 58547731, compound → HCID 58547757, compound

HRID 2207845Notes

Reaction equation

HRID 2207845 reaction equation
Br[C:2]1[C:3]([O:16][CH:17]2[CH2:20][N:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH2:18]2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1>CO.[Pd]>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[N:19]1[CH2:20][CH:17]([O:16][C:3]2[CH:2]=[CH:7][N:6]=[C:5]([N:8]3[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]3)[N:4]=2)[CH2:18]1

Participants

4

Reactant 1

HCID 58547731HCID 58547731, compound

Product 1

HCID 58547757HCID 58547757, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1-(5-bromo-4-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrimidin-2-yl)piperidin-4-yl)methanol (see PREPARATION P7.1; 115 mg, 0.25 mmol) and wet Pd—C (50%, 50 mg) in MeOH (10 mL) was stirred under H2 (15 psi) at room temperature for 1.5 hours then the reaction mixture was filtered through CELITE® and washed with MeOH. The filtrate was concentrated in vacuo to give (1-(4-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrimidin-2-yl)piperidin-4-yl)methanol (93 mg, 0.24 mmol, yield 96%). ESI-MS (M+1): 392 calc. for C22H25N5O2 391.

Workup

  1. filtrationthe reaction mixture was filtered through CELITE®
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-113a3ca812c94d9e9a42e5581d782406
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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