Cesium carbonate → HCID 71506778, compound

HRID 929359Notes

Reaction equation

HRID 929359 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][C:37]1[NH:38][CH:39]=[CH:40][N:41]=1.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]([N:38]2[CH:39]=[CH:40][N:41]=[C:37]2[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:24])=[O:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 86677184HCID 86677184, compound

Product 1

HCID 71506778HCID 71506778, compoundYield 73%

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-methyl-1H-imidazole (18 mg, 24 mmol, 2.5 eq.) and Cs2CO3 (59 mg, 19.2 mmol, 2.0 eq.). The resulting mixture was stirred at 90° C. for 4 h, then 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 (DCM/MeOH-30/1, v/v) to afford N-(2,4,5-trifluoro-3-(3-(2-methyl-1H-imidazol-1-yl)quinoxaline-6-carbonyl)phenyl)propane- 1-sulfonamide (34 mg, 73%). LRMS (M+H+) m/z calculated 490.1, found 489.9. 1H NMR (DMSO, 400 MHz) δ 10.13 (brs, 1 H), 9.46 (s, 1 H), 8.56 (s, 1 H), 7.95 (s, 1 H), 8.36 (brs, 2 H), 7.77 (m, 1 H), 7.94 (s, 1 H), 2.69 (s, 3 H), 3.21 (m, 2 H), 1.75 (m, 2 H), 0.97 (s, 3 H).

Workup

  1. washwashed with water
  2. extractionextracted with EA (20 mL×3)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (DCM/MeOH-30/1

Sources & evidence

ORD record
ord-08d7c67bc1ed4a0a9f7429389ae7cf0c
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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