Hydrochloric Acid → HCID 90428035, compound

HRID 2278978Notes

Reaction equation

HRID 2278978 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20]C(=O)OC(C)(C)C)=[N:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)[O:4][N:3]=1.Cl>C1COCC1>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733475HCID 131733475, compound

Product 1

HCID 90428035HCID 90428035, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of tert-butyl (5-((2-(3-methylisoxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamate (0.30 g, 0.84 mmol) in THF (5 mL) was treated with HCl (3 M, 2.8 mL, 8.4 mmol), heated at 55° C. for 4 h, then cooled to RT and concentrated to dryness. The residue was treated with NaHCO3, EtOAc and water, the layers separated and the aqueous layer extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 5-((2-(3-methylisoxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.24 g, 106%). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (d, J=5.6 Hz, 1 H), 7.84 (br s, 1 H), 7.32 (m, 2 H), 6.95 (m, 2 H), 6.53 (d, J=9.2 Hz, 1 H), 6.07 (br s, 2 H), 2.28 (s, 3 H); MS (ESI) m/z: 269.1 (M+H+).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated to dryness
  3. additionThe residue was treated with NaHCO3, EtOAc and water
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with EtOAc (2×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bddd46f43ed94ed79d4ab5e74e9c1f49
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

Loading…