Dimethyl Sulfoxide → 4-Chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinoline-6-carbaldehyde

HRID 540246Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][OH:23])[CH:20]=2)[N:15]=[C:14]([N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[S:27](=[O:36])(=[O:35])[CH2:26][CH2:25]2)[CH:13]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=[O:23])[CH:20]=2)[N:15]=[C:14]([N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[S:27](=[O:36])(=[O:35])[CH2:26][CH2:25]2)[CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl dichloride (36.3 mg, 0.29 mmol) in dichloromethane (10 mL) was added a solution of dimethyl sulphoxide (0.1 mL, 0.57 mmol) in dichloromethane (10 mL) at −78° C. dropwise. After the mixture being stirred for 10 minutes at −78° C., a solution of 4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol (100 mg, 0.26 mmol, prepared in analogy to the one in Example 3-23) in dichloromethane (5 mL) was added dropwise. After the mixture being stirred for further 1 hour at −78° C., triethylamine (0.2 mL, 1.3 mmol) was. The resulting mixture was stirred at −78° C. for 1 hour and then at room temperature for further 1 hour. The reaction was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 70 mg of the product.

Workup

additionwas added dropwise
stirringAfter the mixture being stirred for further 1 hour at −78° C.
stirringThe resulting mixture was stirred at −78° C. for 1 hour
waitat room temperature for further 1 hour
washThe reaction was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b343c14ea5604fed8f43ae83b3e4be70
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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