HCID 58243441, compound → HCID 58243392, compound

HRID 2361680Notes

Reaction equation

HRID 2361680 reaction equation
[CH3:1][Mg+].[Br-].[CH:4]1([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([N:17]3[CH2:20][CH:19]([O:21][C:22]4[CH:23]=[CH:24][C:25]([C:28]([O:30]CC)=O)=[N:26][CH:27]=4)[CH2:18]3)=[O:16])[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5]1>C(OCC)C>[CH:4]1([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([N:17]3[CH2:18][CH:19]([O:21][C:22]4[CH:23]=[CH:24][C:25]([C:19]([OH:21])([CH3:20])[CH3:18])=[N:26][CH:27]=4)[CH2:20]3)=[O:16])[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5]1.[CH:4]1([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([N:17]3[CH2:18][CH:19]([O:21][C:22]4[CH:23]=[CH:24][C:25]([C:28](=[O:30])[CH3:1])=[N:26][CH:27]=4)[CH2:20]3)=[O:16])[CH2:10][CH2:9]2)[CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 58243441HCID 58243441, compoundHCID 178418689HCID 178418689, compound

Product 2

HCID 58243392HCID 58243392, compoundYield 37%HCID 58243434HCID 58243434, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

MeMgBr (0.96 ml of a 3M solution in diethyl ether, 2.88 mmol) was added dropwise to a solution of ethyl 5-({1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}oxy)pyridine-2-carboxylate (386 mg, 0.96 mmol) in diethyl ether (20 ml) at 0° C. The reaction was warmed to room temperature and after 1 hour was quenched and washed with water (2×20 ml), dried (MgSO4) and concentrated under reduced pressure. The crude material was purified by preparative HPLC to give the title compound (179 mg, 37%) as colourless oil and 1-[5-({1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}oxy)pyridin-2-yl]ethanone (2.5 mg, 1%) as colourless oil.

Workup

  1. customwas quenched
  2. washwashed with water (2×20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-8ae5c63945624258805cccf95c8347d8
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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