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 1817376노트

반응식

HRID 1817376 반응식
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]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 69058481HCID 69058481, 화합물HCID 178418918HCID 178418918, 화합물HCID 178484889magnesium;dimethylazanide;chloride

생성물 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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
-7.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a58cb83ae4ca4b42a4fe93852ab14de2
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598264B2

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