Dimethylamine → 6-[(3-chloro-4-fluoro-phenyl)methyl]-4-hydroxy-N,N,2-trimethyl-3,5-dioxo-7,8-dihydro-2,6-naphthyridine-1-carboxamide

HRID 1817376ノート

反応式

HRID 1817376 の反応式
C([Mg]Cl)(C)C.[CH3:6][NH:7][CH3:8].[Mg](N(C)C)Cl.[Cl:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:18][N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([OH:35])[C:23](=[O:34])[N:24]([CH3:33])[C:25]=2[C:29]([O:31]C)=O)[C:20]1=[O:36]>ClCCl.C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[F:40])[CH2:18][N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([OH:35])[C:23](=[O:34])[N:24]([CH3:33])[C:25]=2[C:29]([N:7]([CH3:8])[CH3:6])=[O:31])[C:20]1=[O:36]

参加物

7

反応物 4

HCID 674DimethylamineHCID 69058481HCID 69058481、化合物HCID 178418918HCID 178418918、化合物HCID 178484889magnesium;dimethylazanide;chloride

生成物 1

HCID 546922716-[(3-chloro-4-fluoro-phenyl)methyl]-4-hydroxy-N,N,2-trimethyl-3,5-dioxo-7,8-dihydro-2,6-naphthyridine-1-carboxamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-7.5 °C

実験手順

To THF (80 mL) cooled to −10° C. was added iPrMgCl (2M in THF, 60 mL). Dimethylamine (2M in THF) was then added at −10 to 0° C., the mixture then stirred for 1 hour at −5 to −10° C. The resulting suspension of ClMgNMe2 at −10° C. was allowed to warm to 0° C., and a solution of methyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (10.0 g) in dichloromethane (100 mL) was added over 20 minutes at 0° C. The mixture was then stirred until reaction was complete by HPLC. The reaction mixture was quenched with 1N HCl (335 mL). The organic layer was collected and the aqueous layer extracted with CH2Cl2 (35 mL). The organic phases were then combined and washed with brine (35 mL). Volatiles were evaporated to give the title product as an amorphous solid.

後処理

  1. temperatureto warm to 0° C.
  2. stirringThe mixture was then stirred until reaction
  3. customThe reaction mixture was quenched with 1N HCl (335 mL)
  4. customThe organic layer was collected
  5. extractionthe aqueous layer extracted with CH2Cl2 (35 mL)
  6. washwashed with brine (35 mL)
  7. customVolatiles were evaporated

出典と根拠

ORDレコード
ord-a58cb83ae4ca4b42a4fe93852ab14de2
出典データセット
uspto-grants-2009_10
特許番号
US07598264B2

反応ノート

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