2-Methoxyethanol → HCID 71505850, compound

HRID 929360Notes

Reaction equation

HRID 929360 reaction equation
Cl[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([C:14]1[C:15]([F:35])=[C:16]([N:22](S(CCC)(=O)=O)[S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH:17]=[C:18]([F:21])[C:19]=1[F:20])=[O:13])=[CH:7][CH:6]=2.[CH3:36][O:37][CH2:38][CH2:39][OH:40].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:35][C:15]1[C:14]([C:12]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]=[CH:3][C:2]([O:40][CH2:39][CH2:38][O:37][CH3:36])=[N:11]3)=[O:13])=[C:19]([F:20])[C:18]([F:21])=[CH:17][C:16]=1[NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 86677184HCID 86677184, compound

Product 1

HCID 71505850HCID 71505850, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(3-(3-chloroquinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)-N-(propylsulfonyl)propane-1-sulfonamide (50 mg, 9.6 mmol, 1.0 eq.) in DMF (2 mL) was added 2-methoxyethanol (17.5 mg, 24 mmol, 2.5 eq.) and Cs2CO3 (87 mg, 24 mmol, 2.0 eq.). The resulting mixture was stirred at 90° C. for 7.5 h, then cooled, washed with water and extracted with EA (20 mL×3). The combined organic phase was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=4/1, v/v) to afford N-(2,4,5-trifluoro-3-(3-(2-methoxyethoxy)quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (28 mg, 61%). LRMS (M+H+) m/z calculated 484.1, found 483.9. 1H NMR (DMSO-d6, 400 MHz) δ10.12 (s, 1 H), 8.81 (s, 1 H), 8.26 (s, 1 H), 8.22 (d, 1 H), 8.15 (d, 1 H), 7.79 (m, 1 H), 4.58 (brs, 2 H), 3.75 (brs, 2 H), 3.33 (s, 3 H), 3.23 (m, 2 H), 1.75 (m, 2 H), 0.97 (s, 3 H).

Workup

  1. temperaturecooled
  2. washwashed with water
  3. extractionextracted with EA (20 mL×3)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography (PE/EA=4/1

Sources & evidence

ORD record
ord-22596d6704a4442eb4a24af8a312c10e
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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