Hydrochloric Acid → HCID 59200479, compound

HRID 1685341Notes

Reaction equation

HRID 1685341 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[C:12]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:11]=[CH:10][N:9]=2)=[N:4][CH:3]=1.[SH:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([O:32]C)=[O:31])[CH:25]=1.C[O-].[Na+].[OH-].[Na+].Cl>CO.CN(C)C=O>[OH:15][CH2:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]2[S:6][C:2]([S:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([C:30]([OH:32])=[O:31])[CH:25]=3)=[CH:3][N:4]=2)[CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 59200468HCID 59200468, compoundHCID 178498628HCID 178498628, compound

Product 1

HCID 59200479HCID 59200479, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 5-bromo-N-(4-((tert-butyldimethylsilyloxy)methyl)pyridine-2-yl)thiazol-2-amine (0.907 g, 2.27 mmol, described in the synthesis of bromides or thioisocyanates, Example A) in methanol (15 mL) was treated with the previously prepared solution of methyl 4-mercaptopicolinate in N,N-dimethylformamide and sodium methoxide (1.47 mL, 25% in MeOH, 6.3 mmol). The reaction was stirred at 65° C. for 1 hour. The solvent was then evaporated and the residue was dissolved in ethyl acetate/tetrahydrofuran. The reaction was acidified with 1N hydrochloric acid and the solvents were evaporated. The crude residue was then diluted in methanol (10 mL) and treated with sodium hydroxide (5N, 4.5 mL, 22.7 mmol) at 23° C. and the reaction was stirred overnight. The reaction was then acidified with 1N hydrochloric acid and the solvent was evaporated. The residue was dissolved in N,N-dimethylformamide (8 mL) and precipitated by addition of water. This was allowed to stand at 0° C. The solid was then filtered and dried under high vacuum to give the title material (0.411 g, 50%) as a solid. LC/MS (M+H)+: 361. HPLC ret. time (Condition B): 1.067 min.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate/tetrahydrofuran
  3. customthe solvents were evaporated
  4. additionThe crude residue was then diluted in methanol (10 mL)
  5. stirringthe reaction was stirred overnight
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in N,N-dimethylformamide (8 mL)
  8. customprecipitated by addition of water
  9. customto stand at 0° C
  10. filtrationThe solid was then filtered
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-8b06d682a01d4471a9716e264f0536a6
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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