Dimethylamine → HCID 24803740, compound

HRID 2384922Notes

Reaction equation

HRID 2384922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:35][C:11]3[C:12](=[O:34])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:26][CH2:25][C@@H:24](OS(C)(=O)=O)[CH2:23]5)=[C:18]([O:32][CH3:33])[CH:17]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:36][NH:37][CH3:38]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:35][C:11]3[C:12](=[O:34])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:26][CH2:25][C@H:24]([N:37]([CH3:38])[CH3:36])[CH2:23]5)=[C:18]([O:32][CH3:33])[CH:17]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 86629209HCID 86629209, compound

Product 1

HCID 24803740HCID 24803740, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

Dissolve methanesulfonic acid (R)-1-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenyl}-pyrrolidin-3-yl ester (0.504 g, 0.952 mmol) in 2 M dimethylamine in THF (10 mL). Stir the mixture at 75° C. overnight in a sealed pressure tube. Dilute the mixture with EtOAc (50 mL) and wash with saturated NaHCO3 (2×20 mL) and brine (20 mL). Dry the solution with Na2SO4, filter, and concentrate. Purify the crude material by chromatograghy, eluting with 2% NH3—H2O/50% CH3OH/EtOAc to give 0.293 g (64%) of 2-(4-chloro-phenyl)-6-[4-((S)-3-dimethylamino-pyrrolidin-1-yl)-3-methoxy-phenyl]-6H-thieno[2,3-c]pyridin-7-one.

Workup

  1. washwash with saturated NaHCO3 (2×20 mL) and brine (20 mL)
  2. dry with materialDry the solution with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatograghy
  6. washeluting with 2% NH3—H2O/50% CH3OH/EtOAc

Sources & evidence

ORD record
ord-fc30fc85e6ce46879c492b760bbc0115
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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