Potassium Carbonate → HCID 71255500, compound

HRID 540148Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:16]=3[S:15](=[O:25])(=[O:24])[CH2:14][CH2:13]2)[CH:3]=1.Br[CH2:27][CH2:28][CH2:29][OH:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][C:21]([O:23][CH2:27][CH2:28][CH2:29][OH:30])=[CH:22][C:16]=3[S:15](=[O:25])(=[O:24])[CH2:14][CH2:13]2)[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-(4-chloroquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepin-8-ol 1,1-dioxide (374.0 mg, 1.0 mmol), 3-bromo-propan-1-ol (0.37 mL, 3.0 mmol) and potassium carbonate (415.0 mg, 3.0 mmol) in N,N-dimethylformamide (1.5 mL) was heated with stirring at 70° C. for 2 hours. After being cooled to room temperature, the resulting mixture was extracted with ethyl acetate (150 mL×2). The combined organic layers were washed with water (50 mL×2) and a saturated aqueous ammonium chloride solution (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 421.6 mg of the crude product as a yellow oil which was used for next step without further purification. MS obsd. (ESI+) [(M+H)+] 433.

Workup

temperaturewas heated
temperatureAfter being cooled to room temperature
extractionthe resulting mixture was extracted with ethyl acetate (150 mL×2)
washThe combined organic layers were washed with water (50 mL×2)
dry with materiala saturated aqueous ammonium chloride solution (50 mL×2), dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2c83f9969fc04dd7badaaa7762896a05
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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