Dimethylformamide → N-[(4-chlorophenyl)methyl]-1-methyl-6-(1,4-oxazepan-4-ylmethyl)-4-oxo-quinoline-3-carboxamide

HRID 1067989

반응식

HRID 1067989 반응식
CS(Cl)(=O)=[O:3].[Cl:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3C(=[CH:19][CH:20]=[C:21]([CH2:26]O)[CH:22]=3)N(C)C=2)=[O:14])=[CH:9][CH:8]=1.[N:31]1[C:36](C)=[CH:35][C:34](C)=[CH:33][C:32]=1C.[CH3:40][N:41]([CH:43]=O)[CH3:42]>CN(C1C=CN=CC=1)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3[C:42](=[CH:19][CH:20]=[C:21]([CH2:26][N:31]4[CH2:36][CH2:35][CH2:34][O:3][CH2:33][CH2:32]4)[CH:22]=3)[N:41]([CH3:40])[CH:43]=2)=[O:14])=[CH:29][CH:30]=1

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 15516933N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

생성물 1

HCID 16073862N-[(4-chlorophenyl)methyl]-1-methyl-6-(1,4-oxazepan-4-ylmethyl)-4-oxo-quinoline-3-carboxamide수율 31%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

Methanesulfonyl chloride (0.080 mL) is added to a cold (0° C.) solution of N-(4-chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (330 mg) from Preparation No. 10, DMAP (19.1 mg), and 2,4,6-collidine (0.14 mL) in anhydrous DMF (15.7 mL). The mixture is stirred at room temperature until the starting material is consumed and a solution of 1,4-oxepane (0.963 g) from Preparation No. 33 in anhydrous DMF (3 mL) is added. The reaction mixture is heated to 56° C. for 1.5 h. The mixture is cooled to room temperature and the product is precipitated by addition of water (125 mL). The solid was adsorbed onto silica and purified by column chromatography (eluent 100% CH2Cl2 (1 L), 1% MeOH in CH2Cl2 (2 L), 1.5% MeOH in CH2Cl2 (1 L), 2% MeOH in CH2Cl2 (3 L)). Fractions homogenous by TLC are combined and concentrated to afford 124.5 mg (31%) of the title compound as a white solid.

후처리

  1. customis consumed
  2. customa solution of 1,4-oxepane (0.963 g) from Preparation No
  3. temperatureThe reaction mixture is heated to 56° C. for 1.5 h
  4. temperatureThe mixture is cooled to room temperature
  5. customthe product is precipitated by addition of water (125 mL)
  6. custompurified by column chromatography (eluent 100% CH2Cl2 (1 L), 1% MeOH in CH2Cl2 (2 L), 1.5% MeOH in CH2Cl2 (1 L), 2% MeOH in CH2Cl2 (3 L))
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-27c11d60dbcb4226807ccb1a0fc16785
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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