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

HRID 2395072ノート

反応式

HRID 2395072 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e771f3f386ff4f268896a13d963552a4
出典データセット
uspto-grants-1998_09
特許番号
US05811459

反応ノート

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