Triethylamine → HCID 68510661, compound

HRID 1404937Notes

Reaction equation

HRID 1404937 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15][CH2:14]3)=[O:12])[S:8][C:4]=2[CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].CCN(CC)CC.[OH-].[Na+]>C(Cl)Cl.CO.C1COCC1>[N:13]1([C:11](=[O:12])[CH2:10][S:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH:24]=[CH:23][C:5]=3[N:6]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 59467893HCID 59467893, compound

Product 1

HCID 68510661HCID 68510661, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of compound 49 (170 mg, 0.48 mmol) in dry CH2Cl2 (5 mL) were added methanesulfonyl chloride (78 μL) followed by dropwise addition of Et3N (0.13 mL). The reaction was stirred for 2.5 h under N2 at room temperature. The reaction mixture was diluted with CH2Cl2 (40 mL), washed with 1N HCl (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL). Dried over MgSO4 and filtered. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 4:1) to afford a mixture of mono and bis-sulfonamides (215 mg). To a solution of the mixture of mono and bis-sulfonamides (200 mg) in 3 mL of MeOH and THF (2:1) was added NaOH (38 mg in 0.1 mL of H2O). The reaction was stirred for 45 min. at room temperature. Most of the solvent was evaporated under vacuum, the residue was dissolved in water (15 mL), and extracted with EtOAc. The combined organics were dried over MgSO4 and filtered. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 2:1) to afford 53 as a white solid (120 mg); MS m/z: 434 (M+H)+. Anal. Calcd. For, C19H19N3O3S3.0.1H2O: C, 52.39; H, 4.86; N, 9.65; S, 22.08. Found: 52.06; H, 4.57; N, 9.45; S, 21.80.

Workup

  1. washwashed with 1N HCl (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (EtOAc/hexanes 4:1)
  6. customto afford
  7. stirringThe reaction was stirred for 45 min. at room temperature
  8. customMost of the solvent was evaporated under vacuum
  9. dissolutionthe residue was dissolved in water (15 mL)
  10. extractionextracted with EtOAc
  11. dry with materialThe combined organics were dried over MgSO4
  12. filtrationfiltered
  13. customThe solvent was removed under reduced pressure
  14. customthe product was purified by column chromatography (EtOAc/hexanes 2:1)

Sources & evidence

ORD record
ord-d184cc43bdd0416e951e3c08b19b8150
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

Loading…