Hydrochloric Acid → HCID 136167009, compound

HRID 1617984Notes

Reaction equation

Cl.[OH:2]/[N:3]=[C:4](/[C:33]1[CH:38]=[CH:37][N:36]=[C:35]([CH3:39])[CH:34]=1)\[CH2:5][C@H:6]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH:21]=2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:39][C:35]1[CH:34]=[C:33](/[C:4](=[N:3]/[OH:2])/[CH2:5][C@H:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH:21]=3)=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH:38]=[CH:37][N:36]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrogen chloride solution (4 M in 1,4-dioxane, 0.22 mL, 0.88 mmol) was added to a solution of (R,E)-tert-butyl 4-(4-(3-(hydroxyimino)-3-(2-methylpyridin-4-yl)-1-o-tolylpropyl)-phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (45 mg, 87.9 μmol) in 1,4-dioxane (4 mL). The reaction mixture was heated for 17 h at 50° C., then treated with sat. aq. sodium hydrogen-carbonate solution (4 mL) and partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. The crude material was triturated with ethyl acetate to afford the title compound (20 mg, 55%). Off-white solid, MS (ESI+): m/z=412.4 ([M+H]+).

Workup

custompartitioned between sat. aq. ammonium chloride solution and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude material was triturated with ethyl acetate

Sources & evidence

ORD record: ord-148477fcc0e94a9da01bf05a57b05004
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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