Sodium Hydroxide → N-[4-(diethoxymethyl)benzyl]-N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]-1H-imidazole-2-carboxamide

HRID 68634ノート

反応式

HRID 68634 の反応式
[CH2:1]([O:3][CH:4]([O:27][CH2:28][CH3:29])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][C:14]2[N:15]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:16]=[CH:17][N:18]=2)=[CH:7][CH:6]=1)[CH3:2].[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[C:35](O)=[O:36].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[OH-].[Na+]>ClCCl>[CH2:1]([O:3][CH:4]([O:27][CH2:28][CH3:29])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]([CH2:13][C:14]2[N:15]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:16]=[CH:17][N:18]=2)[C:35]([C:31]2[NH:30][CH:34]=[CH:33][N:32]=2)=[O:36])=[CH:9][CH:10]=1)[CH3:2]

参加物

7

反応物 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 5743211H-Imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 671649171-[4-(diethoxymethyl)phenyl]-N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]methanamine

生成物 1

HCID 67164206N-[4-(diethoxymethyl)benzyl]-N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]-1H-imidazole-2-carboxamide収率 41.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the compound 16 (1.93 g), 1H-imidazole-2-carboxylic acid (773 mg) and diisopropylethylamine (2.97 g) in dichloromethane (15 mL), O-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.62 g) was added under ice cooling. The reaction mixture was stirred at room temperature for 4 hours. To the reaction mixture, an aqueous 1N sodium hydroxide solution (30 mL) was added. The aqueous layer was extracted twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol=1:0→10:1) to obtain the title compound (977 mg) having the following physical properties.

後処理

  1. extractionThe aqueous layer was extracted twice with dichloromethane (50 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=1:0→10:1)

出典と根拠

ORDレコード
ord-d23f21d9a80a41688ce3947f9f4dbf3b
出典データセット
uspto-grants-2014_09
特許番号
US08822459B2

反応ノート

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