Triethylamine → N-(2-Pyridylmethyl)-4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzamide

HRID 2395072노트

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HRID 2395072 반응식
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:14]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 199401P,P-Diphenylphosphinic azideHCID 189739644-[2-(2-Benzyloxy-3-pyridyl)ethyl]benzoic acid

생성물 1

HCID 18973973N-(2-Pyridylmethyl)-4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzoic acid (0.48 g, 1.44 mmol) and 2-aminomethylpyridine (0.189 g, 1.748 mmol) were dissolved in DMF (20 ml) and cooled to 0° C. Triethylamine (0.15 g, 1.5 mmol) was added followed by diphenylphosphorylazide (0.41 g, 1.48 mmol). The reaction mixture was stirred under argon and allowed to warm to ambient temperature overnight. The reaction was partitioned between EtOAc/water, the organic phase was washed with aqueous sodium bicarbonate, water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (MeOH/CH2Cl2) followed by recrystallisation from EtOAc/hexane and then from EtOH/water to give the title product.

후처리

  1. temperatureto warm to ambient temperature overnight
  2. customThe reaction was partitioned between EtOAc/water
  3. washthe organic phase was washed with aqueous sodium bicarbonate, water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography (MeOH/CH2Cl2)
  7. customfollowed by recrystallisation from EtOAc/hexane

출처 및 근거

ORD 기록
ord-e771f3f386ff4f268896a13d963552a4
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811459

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