Hydrochloric Acid → HCID 22137417, compound

HRID 1827544Notes

Reaction equation

HRID 1827544 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]C2CCCCO2)=[C:31]([CH3:42])[CH:30]=1)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=1)(=[O:12])=[O:11].Cl>C(O)C.C(=O)(O)[O-].[Na+]>[OH:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:16][CH:15]=2)[S:10]([C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])(=[O:12])=[O:11])=[CH:30][C:31]=1[CH3:42]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22137402HCID 22137402, compound

Product 1

HCID 22137417HCID 22137417, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude 2,4,6-trimethyl-N-[3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide (0.089 g, 0.15 mmol) prepared in Step A in 4 mL ethanol was added 0.8 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 2 days and was diluted with 10 mL saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride (2×10 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/ethyl acetate) to afford 0.040 g of the title compound. MS 509.1 (M+1)+

Workup

  1. washThe aqueous solution was washed with methylene chloride (2×10 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, eluting with 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-f8907e3a84814c328b1f5eab4db93629
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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