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 1817376Notes

Reaction equation

HRID 1817376 reaction equation
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]

Participants

7

Reactant 4

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

Product 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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-7.5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a58cb83ae4ca4b42a4fe93852ab14de2
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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