Sodium Carbonate → HCID 91206831, compound

HRID 1800608Notes

Reaction equation

HRID 1800608 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH2:24])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:25])=[CH:10][C:9]=1[F:26])([CH3:4])([CH3:3])[CH3:2].[CH:28]1([C:31](Cl)=[O:32])[CH2:30][CH2:29]1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>N1C=CC=CC=1.CO.O1CCCC1>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:31]([CH:28]4[CH2:30][CH2:29]4)=[O:32])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:25])=[CH:10][C:9]=1[F:26])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 91227255Tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}carbamate

Product 1

HCID 91206831HCID 91206831, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}carbamate (1.30 g, 3.16 mmol) in pyridine (20 mL) was added cyclopropanecarbonyl chloride (345 μL, 3.80 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with water (50 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in a mixed solvent of methanol (10 mL)/tetrahydrofuran (10 mL), sodium carbonate (335 mg, 3.16 mmol) was added, and the mixture was stirred at room temperature for 17 hr. To the reaction mixture was added aqueous ammonium chloride solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→50/50) to give the title compound (1.22 g, 81%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  2. washThe organic layer was washed successively with water (50 mL) and saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionwas added
  6. stirringthe mixture was stirred at room temperature for 17 hr
  7. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  8. washThe organic layer was washed with saturated brine (20 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→50/50)

Sources & evidence

ORD record
ord-1b5c70fdddf84ec3803d2a35994b6423
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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