Hydrochloric Acid → HCID 57504925, compound

HRID 2060801Notes

Reaction equation

HRID 2060801 reaction equation
[ClH:1].[NH2:2][C:3]1[S:4][CH2:5][C@@H:6]2[CH2:11][O:10][CH2:9][C@:7]2([C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=3)[CH:15]=[C:16]([F:18])[CH:17]=2)[N:8]=1>ClCCl.[OH-].[Na+].CO>[ClH:1].[ClH:1].[NH2:2][C:3]1[S:4][CH2:5][C@@H:6]2[CH2:11][O:10][CH2:9][C@:7]2([C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=3)[CH:15]=[C:16]([F:18])[CH:17]=2)[N:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57504926HCID 57504926, compound

Product 1

HCID 57504925HCID 57504925, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

The mixture is cooled to room temperature and stirring is continued for 3 days. The mixture is diluted with dichloromethane and aqueous 0.1 M NaOH and is extracted five times with dichloromethane. The combined organic phase is diluted with MeOH to make a homogenous solution, dried over sodium sulfate, filtered, and the solvent is removed under reduced pressure to give a residue that is purified on silica gel with 5% methanol in dichloromethane to give the title compound as the freebase (0.109 g, 51%). Hydrogen chloride is bubbled through the solution of N-(3-((4aS,7aS)-2-amino-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-5-fluorophenyl)-5-fluoropicolinamide (0.109 g, 0.279 mmol) in methanol for approximately 5 min. The solution is then concentrated under reduced pressure and dried on high vacuum to yield the title compound (0.128 g, 51%). ES/MS m/e: 391 (M+1)

Workup

  1. extractionis extracted five times with dichloromethane
  2. additionThe combined organic phase is diluted with MeOH
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customto give a residue that
  7. customis purified on silica gel with 5% methanol in dichloromethane
  8. customto give the title compound as the freebase (0.109 g, 51%)
  9. concentrationThe solution is then concentrated under reduced pressure
  10. customdried on high vacuum

Sources & evidence

ORD record
ord-dccf4fdb087346df99d3c938f6ae8d52
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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