Hydrochloric Acid → HCID 90446486, compound

HRID 718131Notes

Reaction equation

HRID 718131 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][NH:9][C:10]2[N:15]=[C:14]([CH3:16])[C:13]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)[CH:19]=3)=[CH:12][CH:11]=2)C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[NH:9]([C:10]1[N:15]=[C:14]([CH3:16])[C:13]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)[CH:19]=2)=[CH:12][CH:11]=1)[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90427034HCID 90427034, compound

Product 1

HCID 90446486HCID 90446486, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

6-(2-(Diphenylmethylene)hydrazinyl)-2-methyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (9.3 g, 20.19 mmol) was dissolved in toluene (497 mL). Concentrated HCl (134 mL, 1608 mmol) was added and the reaction mixture was stirred for 1.5 h at 110° C., allowed to cool to RT, and stirred for 10 h. The organic phase was removed and the aqueous phase was extracted with toluene (1×100 mL). The combined organics were back extracted with 1 N HCl (1×100 mL). The combined aqueous phases were adjusted to pH ˜11 with 50% NaOH (aq), saturated with solid NaCl, and extracted with EtOAc (3×200 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo to afford 6-hydrazinyl-2-methyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine (4.7 g, 79%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 8.31 (d, J=5.7 Hz, 1H), 8.22 (s, 1H), 7.92 (s, 1H), 7.44 (s, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.64 (d, J=8.8 Hz, 1H), 6.49 (dd, J=5.7, 2.4 Hz, 1H), 4.14 (s, 2H), 3.84 (s, 3H), 2.11 (s, 3H); MS (ESI) m/z: 297.1 (M+H+).

Workup

  1. temperatureto cool to RT
  2. stirringstirred for 10 h
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was extracted with toluene (1×100 mL)
  5. extractionThe combined organics were back extracted with 1 N HCl (1×100 mL)
  6. extractionextracted with EtOAc (3×200 mL)
  7. dry with materialThe combined organics were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8a933f359ad449e9639e53b69543e3b
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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