Sodium Iodide → HCID 131728740, compound

HRID 601526Notes

Reaction equation

HRID 601526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:33])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]5[O:30][CH2:29][CH2:28][NH:27][CH2:26]5)=[C:19]([O:31][CH3:32])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[C:34]([O-])([O-])=O.[K+].[K+].[Na+].[I-].CI>CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:33])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]5[O:30][CH2:29][CH2:28][N:27]([CH3:34])[CH2:26]5)=[C:19]([O:31][CH3:32])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57501761HCID 57501761, compound

Product 1

HCID 131728740HCID 131728740, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 2-(4-chloro-phenyl)-5-[3-methoxy-4-(morpholin-2-ylmethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (460 mg, 0.928 mmol) in dry acetone (3 mL) under nitrogen. Add K2CO3 (321 mg, 1.11 mmol) and NaI (14 mg, 0.092 mmol). Evacuate under vacuum and charge the reaction mixture with nitrogen. Mix well and then add MeI (70 mL, 1.11 mmol). Stir the reaction mixture overnight. Add saturated NH4Cl solution (5 mL) and extract with EtOAc (3×10 mL). Wash the combined organic layers with water (10 mL), dry with Na2SO4, filter, and concentrate. Purify the resulting residue with silica gel chromatography, using 0-10% MeOH/CHCl3 to give the title compound. Dissolve the compound in minimal CH2Cl2 and add HCl/Et2O to make the HCl salt as a yellow-orange solid (74 mg, 15%). MS (ES+) 500.0 (M+1)+.

Workup

  1. customEvacuate under vacuum
  2. additioncharge the reaction mixture with nitrogen
  3. additionMix well
  4. extractionAdd saturated NH4Cl solution (5 mL) and extract with EtOAc (3×10 mL)
  5. washWash the combined organic layers with water (10 mL)
  6. dry with materialdry with Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the resulting residue with silica gel chromatography

Sources & evidence

ORD record
ord-11c0b7e7e0664534aff26a8ec2b6f1a0
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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