Hydrochloric Acid → HCID 22137409, compound

HRID 1827565Notes

Reaction equation

HRID 1827565 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:29][CH:28]=1)[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C2CCCCO2)=[CH:16][CH:15]=1)[CH3:13])(=[O:10])=[O:9].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH:12]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[CH3:13])[C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:31][CH:32]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22137277HCID 22137277, compound

Product 1

HCID 22137409HCID 22137409, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-{1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethyl}-benzenesulfonamide (0.088 g, 0.150 mmol) in absolute ethanol (4.0 mL) was added HCl (1.2N, 0.8 mL). The reaction was stirred at room temperature overnight. The reaction mixture was quenched with sat. sodium bicarbonate solution (ca. 10 mL) and extracted with methylene chloride (2×10 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated. The residue was purified by preparative TLC (SiO2, 10% methanol/ethyl acetate) to afford the title compound (0.007 g, 14.6 μmol). MS 501.4 (M+1)+

Workup

  1. customThe reaction mixture was quenched with sat. sodium bicarbonate solution (ca. 10 mL)
  2. extractionextracted with methylene chloride (2×10 mL)
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (SiO2, 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d80e654ff9fd4746a5d451fcef04659b
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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