Tetrahydrofuran → HCID 10162091, compound

HRID 1247571Notes

Reaction equation

HRID 1247571 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:33]([O-])=O)=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[CH:7]=1.O1CCCC1>C(O)(=O)C.[Fe]>[NH2:33][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=2[CH:25]=1)=[O:12]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 21908377HCID 21908377, compound

Product 1

HCID 10162091HCID 10162091, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

42 mg of 6-[4-(5-fluoro-2-nitrophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-one is dissolved in 1 ml of acetic acid and 1 ml of tetrahydrofuran b, mixed with 22.5 mg of iron powder and stirred for 16 hours at room temperature. It is suctioned off on diatomaceous earth, concentrated by evaporation, the residue is taken up in ethyl acetate and washed with a saturated sodium hydrogen carbon solution. After chromatography on silica gel with hexane/ethyl acetate (1.5+1) and recrystallization from diisopropyl ether, 10 mg of 6-[4-(2-amino-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-one is obtained, flash point 208° C.

Workup

  1. concentrationconcentrated by evaporation
  2. washwashed with a saturated sodium hydrogen carbon solution
  3. customAfter chromatography on silica gel with hexane/ethyl acetate (1.5+1) and recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-71250994e34147d4adfbcb14372a44eb
Source dataset
uspto-grants-2006_10
Patent number
US07129270B2

Reaction notes

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