Sodium hydride → HCID 86273580, compound

HRID 1497725Notes

Reaction equation

HRID 1497725 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:15][C:14](=[O:16])[NH:13][CH:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]=3[CH:23]=2)=[C:5]([CH3:24])[O:4][N:3]=1.[H-].[Na+].Br[CH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CN(C=O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:15][C:14](=[O:16])[N:13]([CH2:28][CH:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[CH:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]=3[CH:23]=2)=[C:5]([CH3:24])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 27732864-(Bromomethyl)oxaneHCID 117600617HCID 117600617, compound

Product 1

HCID 86273580HCID 86273580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3,5-Dimethyl-isoxazol-4-yl)-4-phenyl-3,4-dihydro-benzo[e][1,3]oxazin-2-one (20 mg, 0.06 mmol) is dissolved in DMF 0.5 mL. Sodium hydride (60% w/w, 2.6 mg, 0.065 mmol) is added. The mixture is cooled in an ice bath. 4-bromomethyltetrahydropyran (14 mg, 0.074 mmol) is added and the mixture stirred and allowed to warm to room temperature over night. Sodium hydride (0.5 mg, 0.013 mmol) is added and the mixture stirred at room temperature for a further 3 hours. The mixture is quenched by the addition of water (1 mL). The solvent is removed in vacuo and the residue is purified by preparative HPLC. The product fraction is lyophilized to produce the desired product as a yellow solid.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. stirringthe mixture stirred at room temperature for a further 3 hours
  3. customThe mixture is quenched by the addition of water (1 mL)
  4. customThe solvent is removed in vacuo
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-1ce31823dc7b482c83808e1901ef5fa9
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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