1,2-Dichloroethane → HCID 66679842, compound

HRID 1842576Notes

Reaction equation

[Cl-].[Na+].[Na+].[Na+].[Cl-].[Cl-].[I:7][C:8]1[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[O:11][C:12]=1[C:13]([OH:15])=O.[O-:23][N+:24]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[C:26]([C@H:34]([NH2:36])[CH3:35])[CH:25]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[I:7][C:8]1[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[O:11][C:12]=1[C:13]([NH:36][C@@H:34]([C:26]1[CH:25]=[N+:24]([O-:23])[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:27]=1)[CH3:35])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tri sodium chloride salt of iodo-2-(4-methylphenyl)-1,3-oxazole-5-carboxylic acid (55.2 mg, 0.11 mmol) in DMF (1.1 mL) were added (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (27.9 mg, 0.12 mmol), EDC (36.7 mg, 0.19 mmol), HOAT (7.45 mg, 55.0 μmol) and triethylamine (61 μL, 0.44 mmol). The mixture was stirred at 50° C. After 30 min, the mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (41 mg). MS 517.8 (M+1).

Workup

customthe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-3b5d6932c5244f97b4c0df8b3005eedd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946231B2

Reaction notes

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