Triethylamine → HCID 68003845, compound

HRID 1896943Notes

Reaction equation

HRID 1896943 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[NH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C>COCCOCCOC>[F:13][C:12]([F:15])([F:14])[C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[N:4][CH:3]=[C:2]2[NH:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151417Glycine tert-butyl esterHCID 68003433HCID 68003433, compound

Product 1

HCID 68003845HCID 68003845, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
100 °C

Procedure

Into a 8 mL vial, was placed a solution of 4-chloro-6-(trifluoromethyl)cinnoline (as prepared in the previous step, 260 mg, 1.12 mmol, 1.00 equiv) in 2-methoxyethyl ether (2 mL), tert-butyl 2-aminoacetate (187 mg, 1.12 mmol, 1.10 equiv) and triethylamine (339 mg, 3.36 mmol, 3.00 equiv). The reaction mixture was stirred overnight at 100° C. in an oil bath. The reaction was then quenched by the addition of 4 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate, and the combined organic layers washed with 2×10 mL of brine, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow solid.

Workup

  1. customThe reaction was then quenched by the addition of 4 mL of water
  2. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
  3. washthe combined organic layers washed with 2×10 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-92627fb18850487abb79db6e45b2fdef
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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