Triethylamine → HCID 90417179, compound

HRID 633519Notes

Reaction equation

HRID 633519 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=1[C:12]1[C:20]2[C:15](=[C:16]([O:21][CH3:22])[N:17]=[CH:18][CH:19]=2)[N:14]([CH3:23])[CH:13]=1.[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30].C(N(CC)CC)C.[OH-].[Na+]>ClCCl.O1CCOCC1>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][S:31]([CH2:29][CH3:30])(=[O:33])=[O:32])=[CH:7][C:6]=1[C:12]1[C:20]2[C:15](=[C:16]([O:21][CH3:22])[N:17]=[CH:18][CH:19]=2)[N:14]([CH3:23])[CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 14798Sodium HydroxideHCID 90417231HCID 90417231, compound

Product 1

HCID 90417179HCID 90417179, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 2D (0.05 g, 0.131 mmol), ethanesulfonyl chloride (0.051 g, 0.393 mmol), and triethylamine (0.080 g, 0.787 mmol) in dichloromethane (3 mL) was stirred at ambient temperature for 2 hours. The solvent was removed, and the residue was treated with sodium hydroxide (0.656 mL, 1.31 mmol) and dioxane (3 mL). The reaction mixture was heated at 80° C. for 3 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the title compound.

Workup

  1. customThe solvent was removed
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5b1d14d13847400a9fce6fa1d2ecd1d7
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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