Hydrochloric Acid → HCID 71053036, compound

HRID 869924Notes

Reaction equation

HRID 869924 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:19]3([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:21][CH2:20]3)=[O:18])[N:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl>O1CCOCC1>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2([C:17]([NH:16][C:11]3[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([C:8]4[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=4)[N:10]=3)=[O:18])[CH2:20][CH2:21]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71053037HCID 71053037, compound

Product 1

HCID 71053036HCID 71053036, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(2′-Methoxy-3-methyl-2,3′-bipyridin-6-yl)-1-(4-methoxyphenyl)cyclopropane carboxamide (TFA salt) (˜39 mg, ˜0.10 mmol) was dissolved in 1,4-dioxane (0.6 mL) in a reaction tube. An aqueous 4M HCl (0.27 mL, 1.1 mmol) was added and the reaction mixture was stirred at 90° C. for 1 hour. The resulting material was cooled to room temperature, filtered, and purified by reverse phase preparative HPLC to yield 1-(4-methoxyphenyl)-N-(5-methyl-6-(2-oxo-1,2-dihydropyridin-3-yl)pyridin-2-yl)cyclo-propanecarboxamide. ESI-MS m/z calc. 375.2. found 376.7 (M+1)+. Retention time 1.26 minutes. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (s, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.47-7.42 (m, 3H), 7.38 (dd, J=6.8, 2.1 Hz, 1H), 6.98 (d, J=8.7 Hz, 2H), 6.25 (t, J=6.6 Hz, 1H), 3.77 (s, 3H), 2.08 (s, 3H), 1.52-1.49 (m, 2H), 1.13-1.11 (m, 2H).

Workup

  1. temperatureThe resulting material was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-dfaf778aa737442f89e2558198aa1fe4
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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