2-Cyclohexylacetyl isothiocyanate → 2-Cyclohexyl-N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)acetamide

HRID 1710998

反応式

HRID 1710998 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH2:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12.[CH:25]1([CH2:31][C:32]([N:34]=[C:35]=[S:36])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C1COCC1>[CH:25]1([CH2:31][C:32]([NH:34][C:35](=[S:36])[NH:24][C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]4[CH:15]=[C:16]([C:18]5[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=5)[S:17][C:10]=34)=[C:2]([F:1])[CH:3]=2)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

参加物

4

反応物 2

HCID 218904982-Cyclohexylacetyl isothiocyanateHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

生成物 1

HCID 866041882-Cyclohexyl-N-(3-fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)acetamide収率 36.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 219 (50 mg, 0.145 mmol) in THF (1.5 mL) was added 2-cyclohexylacetyl isothiocyanate (40 mg, 0.22 mmol) [P. A. S. Smith and R. O. Kan. J. Org. Chem., 1964, 2261] and the reaction mixture was stirred for 3 hours transferred onto a flash chromatography column and eluted with EtOAc-MeOH mixture (19:1), to afford title compound 220a (27.5 mg, 31% yield) as a light yellow solid. Characterization of 220a is provided in the table 21.

後処理

  1. washeluted with EtOAc-MeOH mixture (19:1)

出典と根拠

ORDレコード
ord-6c63248f0b6f4a97b3162c97e46f8730
出典データセット
uspto-grants-2010_09
特許番号
US07790729B2

関連ノート

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