1,2-Dichloroethane → HCID 71522361, compound

HRID 1430585Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C@@H:10]2[CH2:15][CH2:14][C@@H:13]([CH3:16])[NH:12][CH2:11]2)=[N:6][CH:7]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[CH3:31][C:32]1[CH:33]=[CH:34][C:35]([N:41]2[N:45]=[CH:44][CH:43]=[N:42]2)=[C:36]([CH:40]=1)[C:37](O)=[O:38].C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C@H:10]2[CH2:11][N:12]([C:37]([C:36]3[CH:40]=[C:32]([CH3:31])[CH:33]=[CH:34][C:35]=3[N:41]3[N:45]=[CH:44][CH:43]=[N:42]3)=[O:38])[C@H:13]([CH3:16])[CH2:14][CH2:15]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 5-fluoro-2-{[(3S,6R)-6-methylpiperidin-3-yl]ethynyl}pyridine (193 mg, 0.884 mmol), EDC (339 mg, 1.77 mmol), HOAT (241 mg, 1.77 mmol), and 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (216 mg, 1.06 mmol) in DMF (6 mL) was treated with triethylamine (0.37 mL, 2.7 mmol) and the reaction stirred at 50° C. for 2 d. The reaction was diluted with sat'd, aqu. NaHCO3 and extracted twice with EtOAc. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0-65% EtOAc in hexanes to provide the pure title compound as an off-white foam. The pure material gave a high resolution mass spectrum (ES+) m/z of 404.1883, calculated for M+H+ [C23H22FN5O: 404.1881] and a proton NMR spectra consistent with theory.

Workup

additionThe reaction was diluted with sat'd, aqu
extractionNaHCO3 and extracted twice with EtOAc
washThe organics were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel flash chromatography
washeluting with 0-65% EtOAc in hexanes

Sources & evidence

ORD record: ord-0adc961522664969ad6199a1093c9dbc
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940898B2

Reaction notes

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