Ethyl orthoformate → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide

HRID 1593787ノート

反応式

HRID 1593787 の反応式
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[CH2:17](OC(OCC)OCC)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[O:36][CH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]1>C(O)(C)C>[C:1]([C:3](=[CH:17][NH:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[C:30]([O:36][CH2:37][CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)[CH:31]=1)[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2]

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 589997944-Methoxy-3-[3-(4-methylpiperazin-1-yl)propoxy]aniline

生成物 1

HCID 693108472-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide収率 93%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.75 g, 6.75 mmol) in 8.2 mL of iso-propanol was added triethylorthoformate (1.5 g, 10.1 mmol). The mixture was heated to reflux. After 20 minutes, 4-methoxy-3-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenylamine in 20 mLs of iso-propanol was added dropwise so as to maintain reflux. After 26 hours, the reaction was cooled to room temperature and the suspended solids were filtered. The solids were rinsed with iso-propanol until effluent was colorless. The yellow solid was dried in vacuo to give 3.45 g (93%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{4-methoxy-3-[3-(4-methylpiperazin-1-yl)-propoxy]-phenylamino}-acrylamide as a mixture of isomers. 1H NMR (300 MHz, CDCl3) δ 11.35 (br d, 1H), 8.17 (m, 2H), 7.76 (d, 1H), 7.41 (s, 1H), 6.88 (m, 1H) 6.69 (m, 2H), 4.10 (t, J=7 Hz, 2H), 3.96 (s, 3H), 3.87 (s, 3), 2.55 (t, J=7 Hz, 2H), 2.48 (m, 8H), 2.29 (s, 3H), 2.06 (m, 2H); MS (ES) m/z548.1 (M+)

後処理

  1. temperatureThe mixture was heated to reflux
  2. temperatureto maintain
  3. temperaturereflux
  4. waitAfter 26 hours
  5. filtrationthe suspended solids were filtered
  6. washThe solids were rinsed with iso-propanol until effluent
  7. customThe yellow solid was dried in vacuo

出典と根拠

ORDレコード
ord-fc9bbdfc89d94943949400054f3b3c39
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

反応ノート

読み込み中…