2-{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester → 5-Aminomethyl-2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzoic acid methyl ester

HRID 1592650ノート

反応式

HRID 1592650 の反応式
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]([CH2:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1>N.[Ni]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([CH2:10][NH2:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]([CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][N:24]=1

参加物

4

反応物 1

HCID 672726592-{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester

生成物 1

HCID 672731765-Aminomethyl-2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzoic acid methyl ester収率 47.6%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 222Ammonia溶媒

実験手順

A mixture of 2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester (0.37 g, 0.92 mmol) in NH3 saturated MeOH (10 mL) was treated with Raney nickel (0.50 g), and placed under 50 psi H2 on a Parr shaker, for 18 h. The mixture was filtered through celite and the cake was washed with methanol. The eluant was concentrated under reduced pressure. Purification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2-MeOH—NH4OH) provided 0.177 g (47%) of 5-aminomethyl-2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzoic acid methyl ester as a yellow oil.

後処理

  1. filtrationThe mixture was filtered through celite
  2. washthe cake was washed with methanol
  3. concentrationThe eluant was concentrated under reduced pressure
  4. customPurification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2-MeOH—NH4OH)

出典と根拠

ORDレコード
ord-74ddb1be39ab467a9f0120d309993134
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

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