Cyclopropanecarbonyl chloride → Tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate

HRID 1800400Notes

Reaction equation

HRID 1800400 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[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH2:24])[N:23]=3)[CH:20]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>CN(C)C(=O)C.C(OCC)(=O)C>[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[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH:24][C:29]([CH:26]4[CH2:28][CH2:27]4)=[O:30])[N:23]=3)[CH:20]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57749279Tert-butyl {3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}carbamate

Product 1

HCID 91093183Tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamateYield 99.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of tert-butyl{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]phenyl}carbamate (1.5 g, 4.39 mmol) in N,N-dimethylacetamide (5.0 mL) was added cyclopropanecarbonyl chloride (480 μL, 5.27 mmol) under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (1.79 g, 99%) as a pale-yellow oil. The obtained compound was used for the next reaction without further purification.

Workup

  1. temperaturecooling
  2. washwashed with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f37bf969a8fc49b18f072d28a25fea95
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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