Hydrochloric Acid → 1-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)pyrrolidine-2,5-dione

HRID 1797318

反応式

HRID 1797318 の反応式
C(OC(Cl)=O)C(C)C.[Cl:9][C:10]1[CH:11]=[C:12]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][C:33](=[O:39])[CH2:34][CH2:35][C:36]([OH:38])=O)[CH:13]=[CH:14][C:15]=1[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].CN1CCOCC1.C(N(C(C)C)C(C)C)C.Cl>C1COCC1.CCOC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[C:36](=[O:38])[CH2:35][CH2:34][C:33]2=[O:39])[CH:13]=[CH:14][C:15]=1[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

生成物 1

HCID 221744561-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)pyrrolidine-2,5-dione

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-15 °C

実験手順

Iso-butylchloroformate (60 μL, 0.46 mmol) was added to a stirred solution of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746) and 4-methylmorpholine (51 μL, 0.46 mmol) in THF (5.0 mL) at −15° C. After 5 min at 0° C. the reaction mixture was cooled to −15° C. and a solution of ethyl diisopropyl amine (65 μL, 0.46 mmol) in THF (5.0 mL) was added. The resulting reaction mixture was kept at 0° C. for 1 h. The reaction mixture was stirred for 16 h at RT and then poured into a mixture of 1 M HCl(aq) and EtOAc. The organic phase was washed with more HCl(aq)(×2). The organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/EtOAc 1:2 as the eluent to afford the title compound as an oil.

後処理

  1. customThe resulting reaction mixture
  2. washThe organic phase was washed with more HCl(aq)(×2)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-76dee2b40dd6468d9a349eeade00fdd4
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

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