Water → HCID 117667268, compound

HRID 712668Notes

Reaction equation

HRID 712668 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.Br[CH2:22][CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(N(C)C)=O>[O:26]1[CH2:27][CH2:28][CH:23]([CH2:22][O:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:9]=[C:10]4[C:15](=[N:16][CH:17]=3)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]4)[CH:5]=[N:6][CH:7]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27732864-(Bromomethyl)oxaneHCID 117667108HCID 117667108, compound

Product 1

HCID 117667268HCID 117667268, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-(5-hydroxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (25 mg, 0.092 mmol) in DMA (1 mL) is added 4-(bromomethyl)tetrahydropyran (20 mg, 0.11 mmol) and cesium carbonate (36 mg, 0.11 mmol). The resultant mixture is stirred at 70° C. for 16 h. Water is added and the mixture is extracted with EtOAc. The organic layers are combined, washed with brine and dried (Na2SO4). The solvent is evaporated and the crude product is purified by silica gel column eluting (0-10% MeOH in DCM) to afford the title compound (17 mg).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is evaporated
  5. customthe crude product is purified by silica gel column
  6. washeluting (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-6519ef5805c94580abf633264a12ea3e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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