1,2-Dichloroethane → (E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide

HRID 2097061ノート

反応式

HRID 2097061 の反応式
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][NH:13][CH3:14])[CH3:2].C(N(C(C)C)C(C)C)C.Cl.[O:25]=[C:26]1[NH:32][C:31]2[N:33]=[CH:34][C:35]([CH:37]=[CH:38][C:39]([OH:41])=O)=[CH:36][C:30]=2[CH2:29][NH:28][CH2:27]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][N:13]([CH3:14])[C:39](=[O:41])/[CH:38]=[CH:37]/[C:35]1[CH:34]=[N:33][C:31]2[NH:32][C:26](=[O:25])[CH2:27][NH:28][CH2:29][C:30]=2[CH:36]=1)[CH3:2]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59277558(3-Ethyl-benzofuran-2-ylmethyl)methylamineHCID 669665093-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

生成物 1

HCID 16659825(E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide収率 37.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of (3-ethyl-benzofuran-2-ylmethyl)methylamine (185 mg, 0.979 mmol) and (i-Pr)2EtN (0.427 mL, 2.44 mmol) in DMF (25 mL) was treated successively with 3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride (250 mg, 0.816 mmol), HOBt (115 mg, 0.856 mmol), and EDC (316 mg, 2.44 mmol). After stirring overnight at room temperature, the mixture was diluted with water and then extracted with EtOAc (3×). The combined organics were washed with brine and dried, filtered and concentrated in vacuo. Purification by column chromatography (silica gel, CH2Cl2/CH3OH, 40:2 to 35:2) gave the title compound (125 mg, 37%) as a yellow solid: ESI MS m/z 405 (M+H)+.

後処理

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organics were washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography (silica gel, CH2Cl2/CH3OH, 40:2 to 35:2)

出典と根拠

ORDレコード
ord-211320ae8ff247a1b8fbae586d5a31f0
出典データセット
uspto-grants-2013_05
特許番号
US08450307B2

反応ノート

読み込み中…