Triethylamine → HCID 89853822, compound

HRID 931112Notes

Reaction equation

HRID 931112 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=2)[CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([N:34]([O:35][CH3:36])[CH3:33])=[O:11])[N:8]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 252192732-Cyclopropyl-1,3-oxazole-4-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 89853822HCID 89853822, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-cyclopropyloxazole-4-carboxylic acid (0.1 g, 0.653 mmol) in dry dichloromethane (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.25 g, 1.3 mmol) and hydroxybenzotriazole (0.175 g, 1.3 mmol) at 0° C. portion wise. N,O-dimethylhydroxylamine (64 mg, 0.653 mmol) was then added followed by triethylamine (0.26 mL, 1.95 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with ethyl acetate and washed with water and brine solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified by preparative TLC (25% ethyl acetate in petroleum ether) to afford 2-cyclopropyl-N-methoxy-N-methyloxazole-4-carboxamide (100 mg, 83%). MS (ES+) (M+H) 197.25; LCMS retention time: 2.82 min (Method S).

Workup

  1. washwashed with water and brine solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by preparative TLC (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ccf760384c144c1c9205920d570f1e23
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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