Methanol → HCID 71262228, compound

HRID 540154Notes

Reaction equation

HRID 540154 reaction equation
[O:1]=[S:2]1(=[O:30])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:29])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:35]O>>[O:30]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH3:35])=[O:27])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:29])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 71254520HCID 71254520, compound

Product 1

HCID 71262228HCID 71262228, compound

Procedure

To a solution of N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-beta-alanine (85 mg, 0.2 mmol, prepared in analogy to the one in Example 14-2) in methanol (10 mL) at 0° C. was added thionyl chloride (1.5 mL) carefully. The mixture was stirred at room temperature for 20 minutes, and then refluxed at 80° C. for 2 hours. After being cooled to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, water and brine, then dried over sodium sulfate, and concentrated in vacuo to afford the crude product which was directly used for the next step without further purification.

Workup

  1. temperaturerefluxed at 80° C. for 2 hours
  2. temperatureAfter being cooled to room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with a saturated aqueous solution of sodium bicarbonate, water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f15d142b8f0b4b4e9b59a9c20921a483
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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