Pyridine → N-{3-[(4R)-1-hydroxy-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}acetamide

HRID 494582ノート

反応式

HRID 494582 の反応式
Cl.[NH2:2][C:3]1[CH:32]=[CH:31][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:30])[C@:15]([CH3:29])([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:16]4[C:21]([C:22]=3[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].N1C=CC=CC=1>C(Cl)Cl>[OH:23][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@@:15]([CH3:29])([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:14](=[O:30])[C:13]=1[C:8]1[NH:7][C:6]2[CH:31]=[CH:32][C:3]([NH:2][C:33](=[O:35])[CH3:34])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[N:9]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 135869462(1R)-3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methyl-1-(3-methylbutyl)naphthalen-2(1 H)-one hydrochloride

生成物 1

HCID 135409606N-{3-[(4R)-1-hydroxy-4-methyl-4-(3-methylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}acetamide収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of Example 39H (0.050 g, 0.105 mmol), acetic anhydride (0.011 mL, 0.116 mmol), and pyridine (0.068 mL, 0.840 mmol) in methylene chloride (2 mL) was stirred at 25° C. for 4 hours. The solution was concentrated in vacuo and the residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride to give the desired product (0.046 g, 90%). 1H NMR (300 MHz, DMSO-d6): 5 ppm 0.43 (m, 1H) 0.77 (m, 7H) 1.33 (m, 1H) 1.56 (m, 3H) 2.06 (m, 4H) 2.23 (m, 1H) 7.53 (m, 1H) 7.66 (m, 1H) 7.77 (m, 3H) 8.16 (m, 1H) 8.29 (m, 1H) 10.38 (m, 1H) 13.84 (m, 1H).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride

出典と根拠

ORDレコード
ord-ade4d2443c2940d2968f0f8515094bbc
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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