5-Methylsalicylic acid → N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide

HRID 1890136ノート

反応式

HRID 1890136 の反応式
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH2:20][N:19]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH2:18][CH2:17]2.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH2:20][N:19]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[OH:11])[CH2:18][CH2:17]2

参加物

6

反応物 4

HCID 69735-Methylsalicylic acidHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 201155644-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-YL)butan-1-amine

生成物 1

HCID 16738306N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide収率 93%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-methylsalicylic acid (0.691 g, 4.5 mmol), 4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butan-1-amine (1.0 g, 3.8 mmol), N,N′-Dicyclohexylcarbodiimide (DCC) (0.94 g, 4.5 mmol) and 1-Hydroxybenzotriazole hydrate (HOBOt) (0.61 g, 4.5 mmol) in dichloromethane (20 mL) was stirred overnight under an atmosphere of nitrogen. The reaction mixture was washed with saturated sodium bicarbonate solution (3×10 mL). The organic solution was dried over Na2SO4 and volatiles were removed under reduced pressure. The residue was purified by silica gel column with methanol/ether (5/95, v/v) as the mobile phase to afford 4a as a viscous oil (1.39 g; 93%). 1H NMR (300 MHz, CDCl3): 1.70-1.78 (m, 4H), 2.09 (s, 3H), 2.50-2.60 (m, 2H), 2.68-2.76 (m, 2H), 2.78-2.88 (m, 2H), 3.44-3.60 (m, 4H), 3.82 (s, 3H), 3.83 (s, 3H), 6.48 (s, 1H), 6.58 (s, 1H), 6.83-6.87 (d, 1H), 7.00-7.04 (m, 1H), 7.10-7.16 (m, 1H), 7.70-7.90 (s, 1H).

後処理

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution (3×10 mL)
  2. dry with materialThe organic solution was dried over Na2SO4 and volatiles
  3. customwere removed under reduced pressure
  4. customThe residue was purified by silica gel column with methanol/ether (5/95

出典と根拠

ORDレコード
ord-6ac71c7ace6c44569318055fe5c2be55
出典データセット
uspto-grants-2013_08
特許番号
US08506927B2

反応ノート

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