Methylamine → 8-(2-ethyl-6-methylbenzylamino)-N, 2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide

HRID 427485

反応式

HRID 427485 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([OH:23])=O)=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.[CH3:31][N:32](C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.CN>C(Cl)Cl>[CH2:19]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:24]([CH3:25])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[C:7]([C:21]([NH:32][CH3:31])=[O:23])[CH:8]=1)[CH3:20]

参加物

5

反応物 3

HCID 6329MethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

生成物 1

HCID 98632428-(2-ethyl-6-methylbenzylamino)-N, 2,3-trimethylimidazo[1,2-a]pyridine-6-carboxamide収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid (0.15 g, 0.44 mmol) and o-Benzotriazol-1-yl-N,N,N′,N′-Tetramethyluronium tetrafluoroborate (TBTU) (0.14 g, 0.44 mmol) were added to methylene chloride (10 ml) and the reaction mixture was stirred at room temperature for 15 min. Methylamine (0.1 g, 3.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethylacetate:methylene chloride (1:1) as eluent. The yield was treated with diethyl ether to give 40 mg (26%) of the desired product.

後処理

  1. stirringthe reaction mixture was stirred at ambient temperature for 1.5 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. additionThe yield was treated with diethyl ether

出典と根拠

ORDレコード
ord-21e4605fc6fd4ff89efa148354f82356
出典データセット
uspto-grants-2001_11
特許番号
US06313137B1

関連ノート

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