Water → HCID 57388053, compound

HRID 1800621Notes

Reaction equation

HRID 1800621 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([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)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1.O>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:29]([CH:26]4[CH2:28][CH2:27]4)=[O:30])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 57387080HCID 57387080, compound

Product 1

HCID 57388053HCID 57388053, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]phenyl}carbamate (1.00 g, 2.79 mmol) in pyridine (30 mL) was added cyclopropanecarbonyl chloride (327 μL, 3.63 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate (100 mL, 30 mL). The combined organic layer was washed with saturated brine (20 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from tetrahydrofuran and hexane to give the title compound (1.02 g, 86%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL, 30 mL)
  2. washThe combined organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was recrystallized from tetrahydrofuran and hexane

Sources & evidence

ORD record
ord-28c181d402b240ba9918347adca521e8
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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