Triethylamine → HCID 10453790, compound

HRID 227492Notes

Reaction equation

HRID 227492 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl.C(#N)C>[CH3:30][S:31]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 10314224HCID 10314224, compound

Product 1

HCID 10453790HCID 10453790, compound

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of 5-hydroxy-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide from Example 50 (37 mg, 0.12 mmol) in 3 mL of dichloromethane/acetonitrile (1:1) was added triethylamine (0.048 mL, 0.34 mmol) and methanesulfonyl chloride (0.0098 mL, 0.13 mmol). After one hour, another portion of methanesulfonyl chloride (0.005 mL) was added. After another 10 minutes, the mixture was partitioned between ethyl acetate and saturated NH4Cl solution, and the organic layer was washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting solid was triturated with acetonitrile/methanol (1:1) to give the titled compound as a white solid. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C14H18N3O7S2 (M+H+): 404.0581. Found 404.0620.

Workup

  1. waitAfter another 10 minutes
  2. customthe mixture was partitioned between ethyl acetate and saturated NH4Cl solution
  3. washthe organic layer was washed with saturated NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was triturated with acetonitrile/methanol (1:1)

Sources & evidence

ORD record
ord-f109355d719549dd87f34506e4f69f4b
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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