Water → HCID 86679180, compound

HRID 1774828Notes

Reaction equation

HRID 1774828 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:13]=[C:14]([CH2:18][NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:15]=[N:16][CH:17]=3)[CH:8]=2)[NH:3]1.[Cl:25]N1C(=O)CCC1=O.O>CN(C=O)C.CCOC(C)=O>[Cl:25][C:5]1[CH:6]=[C:7]([C:12]2[CH:13]=[C:14]([CH2:18][NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:15]=[N:16][CH:17]=2)[CH:8]=[C:9]2[C:4]=1[NH:3][C:2](=[O:1])[CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 71533571HCID 71533571, compound

Product 1

HCID 86679180HCID 86679180, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethanesulfonic acid [5-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide (example 55, 0.681 g, 0.197 mmol) in DMF (1 mL) heated to 65° C. was added N-chloro-succinimide (0.034 g, 0.256 mmol) and the reaction mixture was stirred at this temperature over night. The mixture was diluted with EtOAc, poured into water (5 mL) and extracted with EtOAc (2×10 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by reverse phase HPLC on a Gemini-NX column, eluting with a MeOH—H2O (0.05% TEA) gradient to give the title compound (0.025 g, 33%) as a colorless amorphous solid. MS: 380.4 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by reverse phase HPLC on a Gemini-NX column
  7. washeluting with a MeOH—H2O (0.05% TEA) gradient

Sources & evidence

ORD record
ord-a671c935948a4d97905f979225e5adb7
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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