1,2-Dimethoxyethane → HCID 91799311, compound

HRID 515545Notes

Reaction equation

HRID 515545 reaction equation
Br[C:2]1[C:3](=[O:28])[NH:4][C:5]2[CH:6]=[C:7]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:8]=[C:9]([S:12]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:14])=[O:13])[C:10]=2[CH:11]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC>O>[CH:16]1([NH:15][S:12]([C:9]2[C:10]3[CH:11]=[C:2]([C:31]4[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=4)[C:3](=[O:28])[NH:4][C:5]=3[CH:6]=[C:7]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:8]=2)(=[O:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27343783-Pyridinylboronic acidHCID 118094077HCID 118094077, compound

Product 1

HCID 91799311HCID 91799311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydroquinoline-5-sulfonamide (45 mg, 0.1 mmol), 3-pyridine boronic acid (25 mg, 0.2 mmol), cesium carbonate (100 mg, 0.3 mmol), Peppsi-iPr (4 mg, 5 mol %), dimethoxyethane (2 mL) and water (1 mL) was stirred at 100° C. for 2 hours. The reaction mixture was concentrated before being purified by preparative HPLC to give N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-(pyridin-3-yl)-1,2-dihydroquinoline-5-sulfonamide as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custombefore being purified by preparative HPLC

Sources & evidence

ORD record
ord-a69a0bd205ec46afb91b1ac37830f704
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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