Triethylamine → 2-acetylamino-4-methyl-thiazole-5-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4 g]quinolin-5-yl ester

HRID 853675ノート

反応式

HRID 853675 の反応式
C(N(CC)CC)C.[C:8]([NH:11][C:12]1[S:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[C:15]([CH3:17])[N:16]=1)(=[O:10])[CH3:9].[CH:22]([O:35][C:36]1[C:37]2[C:49](=[O:50])[N:48]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[CH2:47][C:38]=2[C:39]([OH:46])=[C:40]2[C:45]=1[N:44]=[CH:43][CH:42]=[CH:41]2)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCOC(C)=O.CCCCCC>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:22]([O:35][C:36]1[C:37]2[C:49](=[O:50])[N:48]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[CH2:47][C:38]=2[C:39]([O:46][S:18]([C:14]2[S:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[N:16][C:15]=2[CH3:17])(=[O:19])=[O:20])=[C:40]2[C:45]=1[N:44]=[CH:43][CH:42]=[CH:41]2)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 1361585899-Benzhydryloxy-7-(4-fluoro-benzyl)-5-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

生成物 1

HCID 601076382-acetylamino-4-methyl-thiazole-5-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4 g]quinolin-5-yl ester収率 79%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (50 g), DMAP (catalytic amount) and 2-acetylamino-4-methyl-thiazole-5-sulfonyl chloride (25.5 mg, 0.10 mmol) were added to 0.034 mmol 45. The reaction mixture was stirred at room temperature for 18 hours under an inert atmosphere. The reaction was monitored by TLC (EtOAc/hexane 3/7) (Rf 44=0.5, Rf 45=0, Rf 272=0.2) and LC/MS. After completion of the reaction, the mixture was diluted with EtOAc (20 mL) and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethylacetate/hexane—3/7) to afford 2-acetylamino-4-methyl-thiazole-5-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 272 (18.9 mg, 79%).

後処理

  1. customAfter completion of the reaction
  2. washwashed with 1N HCl, saturated NaHCO3 and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethylacetate/hexane—3/7)

出典と根拠

ORDレコード
ord-3a4b66164e644dcb91ce1178134ad53c
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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