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

HRID 7793

반응식

HRID 7793 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a752199fbaf94b028d6f53b4c6e54495
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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