1,4-Dioxane hydrochloride → HCID 86651790, compound

HRID 241271Notes

Reaction equation

HRID 241271 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH:10]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)=[CH:26][CH:25]=1)[C:11]1[N:16]=[C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])[CH:14]=[CH:13][CH:12]=1)(=[O:9])=[O:8].Cl.O1[CH2:41][CH2:40]OCC1>C(O)CCCCC>[CH2:2]([O:20][C:19](=[O:21])[CH2:18][NH:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:10]([S:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:9])=[O:8])[NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[S:31][CH:32]=[CH:33][N:34]=3)=[CH:26][CH:25]=2)[N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66717287HCID 66717287, compound

Product 1

HCID 86651790HCID 86651790, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

To a solution of (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acid (110 mg, 0.222 mmol) obtained in Example 3-(b) in 1-hexanol (0.83 ml) was added a 4N hydrogen chloride/1,4-dioxane solution (0.83 ml), followed by stirring at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and a saturated aqueous sodium hydrogencarbonate solution was added to the residue, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (119 mg) as a colorless oil. (Yield: 92%)

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-a9bd3e3933f548e79d7fc7fd23bf7e44
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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