Pyridinium chloride → HCID 68517771, compound

HRID 732804Notes

Reaction equation

HRID 732804 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[C:30]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)=[CH:34][CH:33]=2)=[O:31])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>>[ClH:1].[OH:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:30]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][CH2:40][N:41]3[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]3)=[CH:36][CH:37]=1)=[O:31])=[C:18]([C:15]1[CH:14]=[CH:13][C:12]([S:9]([CH3:8])(=[O:11])=[O:10])=[CH:17][CH:16]=1)[CH:27]=[CH:26]2

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 11692407HCID 11692407, compound

Product 1

HCID 68517771HCID 68517771, compoundYield 69%

Conditions

Temperature
200 °C

Procedure

Add pyridine hydrochloride (4.0 g) to the compound of Example 74 (100 mg, 0.18 mmol). Purge the vessel with nitrogen, cap it, and heat to 200° C. for 4 hours. Cool to room temperature and dilute with saturated aqueous NaHCO3. Extract with 25% isopropanol (i-PrOH) in CHCl3, dry over Na2SO4 and concentrate in vacuo. Purify using an SCX column (eluting with 2M NH3/MeOH) followed by flash chromatography (0-10% MeOH/CHCl3). Dissolve the product in 1:1 CH3CN/1M aqueous HCl and lyophilize to yield 70.3 mg of the title compound (68%). LCMS: m/z=530 (M+H)+.

Workup

  1. customPurge the vessel with nitrogen
  2. customcap it
  3. temperatureCool to room temperature
  4. additiondilute with saturated aqueous NaHCO3
  5. extractionExtract with 25% isopropanol (i-PrOH) in CHCl3
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate in vacuo
  8. customPurify
  9. washan SCX column (eluting with 2M NH3/MeOH)
  10. dissolutionDissolve the product in 1:1 CH3CN/1M aqueous HCl and lyophilize

Sources & evidence

ORD record
ord-cec720cecae2474b9a19e8990d076f48
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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