Hydroxyamine hydrochloride → 6-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]pyridin-3-amine

HRID 7793

Reaction equation

HRID 7793 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([N:22]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:18][CH:17]=2)=[C:12]([O:36][CH3:37])[CH:11]=1.CC([O-])=O.[Na+].Cl.NO>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)=[C:12]([O:36][CH3:37])[CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 219909526-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine

Product 1

HCID 101497166-[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine (61 mg, 0.13 mmol) was dissolved in MeOH (2 mL) and NaOAc (25 mg, 0.31 mmol) and hydroxylamine hydrochloride (16 mg, 0.23 mmol) were added. The resulting suspension was stirred at rt for 1 h. The mixture was partitioned between CH2Cl2 and 0.1N aqueous NaOH. Aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]pyridin-3-amine: 1H NMR (CDCl3, 300 MHz) δ 8.25–8.24 (d, 1H), 7.95 (s, 2H), 7.86 (s, 1H), 7.80–7.76 (m, 2H), 7.62–7.59 (m, 1H), 7.38–7.35 (m, 2H), 7.07–7.04 (m, 1H), 4.01 (s, 3H). MS (ESI) 318 (M+H)+.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 0.1N aqueous NaOH
  2. extractionAqueous layer was extracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-a752199fbaf94b028d6f53b4c6e54495
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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