Sodium hydride → HCID 19023220, compound

HRID 1034136Notes

Reaction equation

HRID 1034136 reaction equation
[F:1][C:2]1[C:15]([NH:16][C:17]([O:19]C)=O)=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[NH2:21]/[C:22](/[C:29]([F:32])([F:31])[F:30])=[CH:23]\[C:24]([O:26]CC)=O.[H-].[Na+].[N+:35](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O.O>[NH2:35][N:21]1[C:22]([C:29]([F:30])([F:31])[F:32])=[CH:23][C:24](=[O:26])[N:16]([C:15]2[C:2]([F:1])=[CH:3][C:4]3[O:9][CH2:8][C:7](=[O:10])[N:6]([CH2:11][C:12]#[CH:13])[C:5]=3[CH:14]=2)[C:17]1=[O:19]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 19023224HCID 19023224, compound

Product 1

HCID 19023220HCID 19023220, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (1.4 g) and ethyl 3-amino-4,4,4-trifluorocrotonate was dissolved in dimethylformamide (5 g), and sodium hydride (0.2 g) was added thereto. The resultant mixture was stirred for 30 minutes while cooling with ice and heated under reflux for 3 hours. After cooling, 2,4-dinitrophenoxyamine (1.2 g) was added thereto, and the resultant mixture was stirred at 40° C. for 3 hours. After completion of the reaction, the reaction mixture was combined with water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-amino-1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (0.2 g).

Workup

  1. temperaturewhile cooling with ice
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. customAfter completion of the reaction
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5930d3e283c40e4bffd4ea1fec77ebc
Source dataset
uspto-grants-1994_05
Patent number
US05314864

Reaction notes

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