Triethylamine → HCID 86629209, compound

HRID 2384921Notes

Reaction equation

HRID 2384921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:31][C:11]3[C:12](=[O:30])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]5)=[C:18]([O:28][CH3:29])[CH:17]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:31][C:11]3[C:12](=[O:30])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:26][CH2:25][C@@H:24]([O:27][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:23]5)=[C:18]([O:28][CH3:29])[CH:17]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24803254HCID 24803254, compound

Product 1

HCID 86629209HCID 86629209, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 2-(4-chloro-phenyl)-6-[4-((R)-3-hydroxy-pyrrolidin-1-yl)-3-methoxy-phenyl]-6H-thieno[2,3-c]pyridin-7-one (2.407 g, 5.34 mmol) in CH2Cl2 (50 mL) and add MsCl (0.46 mL, 5.87 mmol) and Et3N (1.0 mL, 7.32 mmol). Stir the mixture at RT for one hour. Dilute the mixture with CH2Cl2 (50 mL) and wash with water (30 mL). Dry the solution with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 10% EtOAc/CH2Cl2 to give 1.05 g (37%) of the title compound. LC-MS/ES m/z (35Cl) 531.8 [M+H]+.

Workup

  1. washwash with water (30 mL)
  2. dry with materialDry the solution with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography
  6. washeluting with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-9fdac9e2d28e44f68c85ebb1a52fbd4d
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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