Pyridinium chloride → HCID 11519653, compound

HRID 748941Notes

Reaction equation

HRID 748941 reaction equation
[ClH:1].N1C=CC=CC=1.[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:28]C)[CH:24]=3)[C:19]=2[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:33][CH:32]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>>[ClH:1].[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]4[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]4)=[CH:33][CH:32]=3)=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21]3)=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 11649435HCID 11649435, compound

Product 1

HCID 11519653HCID 11519653, compoundYield 80%

Conditions

Temperature
200 °C

Procedure

Add pyridine hydrochloride (4 g) to the compound of Example 77 (110 mg, 0.21 mmol). Purge with nitrogen, cap the vessel and heat to 200° C. for 2 hours. Cool the reaction mixture and dilute with saturated aqueous NaHCO3. Extract with CH2Cl2, dry over Na2SO4, filter and concentrate. Purify the crude product by flash chromatography (0-10% MeOH/CH2Cl2). Dissolve the product in 1:1 CH3CN/1M aqueous HCl and lyophilize to afford 92 mg of the title compound (80%). LCMS: m/z=516 (M+H)+—HCl.

Workup

  1. customPurge with nitrogen
  2. customcap the vessel
  3. temperatureCool the reaction mixture
  4. additiondilute with saturated aqueous NaHCO3
  5. extractionExtract with CH2Cl2
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude product by flash chromatography (0-10% MeOH/CH2Cl2)
  10. dissolutionDissolve the product in 1:1 CH3CN/1M aqueous HCl

Sources & evidence

ORD record
ord-584fcb60b91d41e08f847829daf1170b
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

Loading…