Triethylamine → HCID 86638160, compound

HRID 423430Notes

Reaction equation

HRID 423430 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:29][C:11]3[C:12](=[O:28])[N:13]([C:16]4[CH:17]=[N:18][C:19]([N:22]5[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23]5)=[CH:20][CH:21]=4)[CH2:14][CH2:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:29][C:11]3[C:12](=[O:28])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:26][CH2:25][C@H:24]([O:27][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:23]5)=[N:18][CH:17]=4)[CH2:14][CH2:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66674460HCID 66674460, compound

Product 1

HCID 86638160HCID 86638160, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-6-[6-((S)-3-hydroxy-pyrrolidin-1-yl)-pyridin-3-yl]-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (1.246 g, 2.93 mmol) in CH2Cl2 (25 mL). Cool to 0° C. and treat with Et3N (0.61 mL, 4.39 mmol), followed by MsCl (0.25 mL, 3.22 mmol). Stir at 0° C. for 15 min and at RT for 2 h. Dilute the mixture with CH2Cl2 (50 mL). Wash with H2O (2×40 mL), dry with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 10% CH3OH/CH2Cl2 to give 1.21 g (82%) of the title compound. MS/ES m/z (35Cl) 504.0 [M+H]+.

Workup

  1. washWash with H2O (2×40 mL)
  2. dry with materialdry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography
  6. washeluting with 10% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-5245794461914101bacf4124c9e8f6d6
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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