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

반응식

HRID 551866 반응식
[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]

참가 물질

6

반응물 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

생성물 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]-amide수율 71.9%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-e5aee8ca17184d2890a10070de975e28
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947835B2

연결된 노트

불러오는 중…