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

HRID 427485

반응식

HRID 427485 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-21e4605fc6fd4ff89efa148354f82356
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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