Hydrochloric Acid → HCID 22137291, compound

HRID 1827551Notes

Reaction equation

HRID 1827551 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C3CCCCO3)[CH:14]=2)(=[O:10])=[O:9])=[C:4]([O:40][C:41]([F:44])([F:43])[F:42])[CH:3]=1.Cl>C(O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:28][CH:27]=2)(=[O:9])=[O:10])=[C:4]([O:40][C:41]([F:42])([F:44])[F:43])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22137332HCID 22137332, compound

Product 1

HCID 22137291HCID 22137291, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-bromo-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-2-trifluoromethoxy-benzenesulfonamide (0.106 g, 0.15 mmol) in 4 mL ethanol was added 0.8 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 6 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 0.030 g (29%) of 4-bromo-N-(3-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl)-2-trifluoromethoxy-benzenesulfonamide. MS 617.3 (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-f07d8a3335954c9e9b813528088eed92
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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