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

HRID 7793

反応式

HRID 7793 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-a752199fbaf94b028d6f53b4c6e54495
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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