Triethylamine → HCID 90416610, compound

HRID 633531Notes

Reaction equation

HRID 633531 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[C:4]([C:17]2[C:25]3[C:20](=[C:21]([O:26][CH3:27])[N:22]=[CH:23][CH:24]=3)[N:19]([CH3:28])[CH:18]=2)[CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C.[OH-].[Na+]>ClCCl.O1CCOCC1>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:3][C:4]=2[C:17]2[C:25]3[C:20](=[C:21]([O:26][CH3:27])[N:22]=[CH:23][CH:24]=3)[N:19]([CH3:28])[CH:18]=2)=[CH:8][CH:9]=1)#[N:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 90418161HCID 90418161, compound

Product 1

HCID 90416610HCID 90416610, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 16D (0.03 g, 0.081 mmol), methanesulfonyl chloride (0.028 g, 0.243 mmol), and triethylamine (0.049 g, 0.486 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-3d782376e660449ab4f7442d5d119fca
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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