Triethylamine → N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamide

HRID 572208ノート

反応式

HRID 572208 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH:27]=1)[C:24](O)=[O:25].Cl.CN(C)CCCN=C=NCC.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>ClCCl>[Br:17][C:13]1[N:12]=[C:11]([NH:10][C@H:8]([C:4]2[CH:3]=[C:2]([NH:1][C:24](=[O:25])[C:23]3[CH:27]=[C:19]([CH3:18])[CH:20]=[N:21][CH:22]=3)[CH:7]=[CH:6][CH:5]=2)[CH3:9])[CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 2562085-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86641857N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine

生成物 1

HCID 25218464N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamide収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine (70 mg, 0.24 mmol), 5-methylnicotinic acid (39 mg, 0.29 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol), 4-pyrrolidinopyridine (7 mg, 0.05 mmol) and triethylamine (0.08 mL, 0.58 mmol) in dichloromethane (3 mL) was stirred at room temperature for 17 hours. After this time the mixture was diluted with dichloromethane (20 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give a dark yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamide (62 mg, 63%) as a pale yellow foam.

後処理

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a dark yellow oil which
  5. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-530b5bf968134d24ba1742d7d8f563e4
出典データセット
uspto-grants-2015_05
特許番号
US09029386B2

反応ノート

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