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Dicyclohexylcarbodiimide → 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749470
ノート
印刷プレビュー

反応式

HRID 749470 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:9][NH2:10])=[C:4]([CH3:20])[CH:3]=1.[C:21]([C:23]1[CH:24]=[C:25]([C:33](O)=[O:34])[C:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=2[CH:32]=1)#[N:22].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:21]([C:23]1[CH:24]=[C:25]([C:33]([NH:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:20])[CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[O:34])[C:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:31]=2[CH:32]=1)#[N:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidHCID 68976391[2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amine

生成物 1

HCID 689801273-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide収率 92.3%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

[2-(4-Fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]amine (0.40 g, 1.4 mmol), 3-cyano-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid (see WO 00/34243; 0.32 g, 1.6 mmol) and DCC (0.35 g, 1.7 mmol) were mixed with CH2Cl2 (5 mL). The mixture was stirred at room temperature overnight and then filtrated and the solvent was evaporated. The product was purified by chromatography on silica gel using methanol and CH2Cl2 (0%-2% methanol). There was obtained 600 mg (91%) of 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide as a foam. 1H NMR (500 MHz, CDCl3): 1.0-1.9 (m, 9H), 2.0-2.1 (m, 1H), 2.4 (d, 3H), 2.6-2.8 (m, 4H), 3.2-3.8 (m, 7H), 4.4-4.5 (d, 1H), 6.0-6.2 (m, 1H), 6.9 (m, 2H), 7.1-7.3 (m, 2H), 7.4 (s, 1H). LCMS: m/z 463 (M−1)−.

後処理

  1. filtrationfiltrated
  2. customthe solvent was evaporated
  3. customThe product was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-20a99faf95b84b99b303269d55ab182d
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07402581B2

反応ノート

読み込み中…

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