Ammonium Chloride → 4,5,6,7-Tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{3-amino-4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide

HRID 551866

反応式

HRID 551866 の反応式
[OH:1][CH2:2][CH2:3][N:4]([CH3:44])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:15](=[O:40])[N:16]([CH3:39])[CH:17]=[C:18]([C:20]3[C:21]([CH3:38])=[C:22]([NH:26][C:27]([C:29]4[S:33][C:32]5[CH2:34][CH2:35][CH2:36][CH2:37][C:31]=5[CH:30]=4)=[O:28])[CH:23]=[CH:24][CH:25]=3)[N:19]=2)=[CH:9][C:8]=1[N+:41]([O-])=O)=[O:6].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:41][C:8]1[CH:9]=[C:10]([NH:13][C:14]2[C:15](=[O:40])[N:16]([CH3:39])[CH:17]=[C:18]([C:20]3[C:21]([CH3:38])=[C:22]([NH:26][C:27]([C:29]4[S:33][C:32]5[CH2:34][CH2:35][CH2:36][CH2:37][C:31]=5[CH:30]=4)=[O:28])[CH:23]=[CH:24][CH:25]=3)[N:19]=2)[CH:11]=[CH:12][C:7]=1[C:5](=[O:6])[N:4]([CH2:3][CH2:2][OH:1])[CH3:44]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 587289644,5,6,7-Tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-3-nitro-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide

生成物 1

HCID 587291034,5,6,7-Tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{3-amino-4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide収率 71.9%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

4,5,6,7-Tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-3-nitro-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide (5) (200 mg, 0.32 mmol) is dissolved in a mixture of ethanol (25 mL) and water (5.0 mL). Ammonium chloride (200 mg, 3.81 mmol) and iron powder (200 mg, 3.58 mmol) are then added and the reaction is allowed to proceed at 95° C. for 30 min. The reaction contents are then hot-filtered through celite and then transferred to a seperatory funnel with ethyl acetate (100 mL). The crude solution is then washed with saturated sodium bicarbonate (1×100 mL), then washed with saturated sodium chloride (1×100 mL) and dried over sodium sulfate. The solution is then filtered and concentrated under reduced pressure. The resulting residue is then triturated with DCM and ethyl ether to give 4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid [3-(6-{3-amino-4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-phenylamino}-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl)-2-methyl-phenyl]-amide (6) as an off-white solid (135 mg), m/z 587.20 (MH+).

後処理

  1. customThe reaction contents
  2. filtrationare then hot-filtered through celite
  3. customtransferred to a seperatory funnel with ethyl acetate (100 mL)
  4. washThe crude solution is then washed with saturated sodium bicarbonate (1×100 mL)
  5. washwashed with saturated sodium chloride (1×100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution is then filtered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is then triturated with DCM and ethyl ether

出典と根拠

ORDレコード
ord-e5aee8ca17184d2890a10070de975e28
出典データセット
uspto-grants-2011_05
特許番号
US07947835B2

関連ノート

読み込み中…