Sodium hydride → HCID 58999590, compound

HRID 1593595Notes

Reaction equation

HRID 1593595 reaction equation
[CH2:1]([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][C:13]([CH3:18])=[C:12]([C:19]([NH2:21])=[O:20])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[C:26]12([CH2:36]Br)[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2>CN(C=O)C>[C:26]12([CH2:36][NH:21][C:19]([C:12]3[C:11]4[CH2:10][CH2:9][N:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:17][C:16]=4[CH:15]=[N:14][C:13]=3[CH3:18])=[O:20])[CH2:27][CH:28]3[CH2:34][CH:32]([CH2:31][CH:30]([CH2:29]3)[CH2:35]1)[CH2:33]2

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 14163041-(Bromomethyl)adamantane2×HCID 58999601HCID 58999601, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58999590HCID 58999590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7-benzyl-5,6,7,8-tetrahydro-3-methyl-2,7-naphthyridine-4-carboxamide (40 mg, 0.142 mmol) was taken up in anhydrous DMF (0.5 ml) under an inert atmosphere. NaH (60% in mineral oil) (6.8 mg, 0.17 mmol) was added to the reaction vessel and the mixture stirred for 30 minutes until the evolution of hydrogen gas ceased. To this mixture was added 1-adamantylmethylbromide in DMF (0.5 ml) and reaction was stirred at room temperature for 4 hr. The reaction was monitored by TLC and LCMS. Excess NaH and 1-adamantylmethylbromide and heated from 40 to 75° C. for 3 days. The mixture was cooled to room temperature, and added to ice water. The aqueous layer was extracted with EtOAc, washed with water, brine, dried over sodium sulfate, and reduced in vacuo. The crude was purified by flash chromatography followed by prep. TLC using MeOH:DCM (5-10%) to afford the title compound. (5 mg, 8%).

Workup

  1. additionTo this mixture was added
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-a8e933049e4d4cac9d867345fd55d30a
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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