Hydrochloric Acid → HCID 90402691, compound

HRID 2278908Notes

Reaction equation

HRID 2278908 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[N:5]=[C:4]([NH:22]C(=O)C)[CH:3]=1.Cl>C1COCC1>[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[N:5]=[C:4]([NH2:22])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90425944HCID 90425944, compound

Product 1

HCID 90402691HCID 90402691, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of N-(4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)acetamide (692 mg, 2.051 mmol) in THF (25 mL) was treated with HCl (3 M, 3.4 mL, 10.2 mmol) and warmed at 40° C. for 17 h. The mixture was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (446 mg, 73%). 1H NMR (400 MHz, DMSO-d6): δ 8.30 (d, J=5.7 Hz, 1 H), 8.23 (s, 1 H), 7.93 (d, J=0.7 Hz, 1 H), 7.10 (d, J=2.4 Hz, 1 H), 6.44 (dd, J=5.7, 2.4 Hz, 1 H), 6.22 (s, 1 H), 5.81 (s, 2 H), 3.84 (s, 3 H), 2.02 (s, 3 H), 1.92 (s, 3 H); MS (ESI) m/z: 296.1 (M+H+).

Workup

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with EtOAc (2×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-b569547d7722418e9c99361af22dea76
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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