Triethylamine → HCID 178464905, compound

HRID 1480140Notes

Reaction equation

[CH3:1][C:2]([NH:8][C:9]([C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([Br:23])=[CH:13][N:12]=1)=[O:10])([C:6]#[N:7])[CH:3]1[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl.[NH2:32][OH:33]>C(O)C>[CH:3]1([C:2]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])[C:14]([Br:23])=[CH:13][N:12]=2)=[O:10])([C:6](=[NH:7])[NH:32][OH:33])[CH3:1])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (methyl-cyano-cyclopropyl-methyl)-amide (Example 78e, 900 mg, 2.29 mmol) in ethanol (15 ml) were added triethylamine (244 mg, 336 μl, 2.41 mmol) and hydroxylamine hydrochloride (167 mg, 2.41 mmol). The reaction mixture was then stirred at 65° C. for 18 hours. Volatiles were removed in vacuo and the residue was dissolved in ethylacetate which was extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (576 mg, 59%) as a white solid. MS (ESI, m/z): 425.3 (M+H+).

Workup

customVolatiles were removed in vacuo
dissolutionthe residue was dissolved in ethylacetate which
extractionwas extracted with an 1.0M aqueous solution of sodium bicarbonate
dry with materialThe organic phase was dried over sodium sulfate
customevaporated down to dryness
customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

Sources & evidence

ORD record: ord-e83fab0e1fbd43bca1ff115efbc27974
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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