Water → 3-(4-Methoxybenzyl)6-fluoro-7-(methylamino)2,3-dihydrobenzo[e][1,3]oxazin-4-one

HRID 1271052Notes

Reaction equation

HRID 1271052 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[C:16]([F:20])[C:17](F)=[CH:18][C:11]=3[O:10][CH2:9]2)=[CH:5][CH:4]=1.[CH3:23][NH2:24].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[C:16]([F:20])[C:17]([NH:24][CH3:23])=[CH:18][C:11]=3[O:10][CH2:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 184524873-(4-Methoxybenzyl)6,7-difluor-2,3-dihydrobenzo[e][1,3]oxazin-4-one

Product 1

HCID 184524883-(4-Methoxybenzyl)6-fluoro-7-(methylamino)2,3-dihydrobenzo[e][1,3]oxazin-4-oneYield 85.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To 3-(4-methoxybenzyl)6,7-difluor-2,3-dihydrobenzo[e][1,3]oxazin-4-one (1.15 g, 3.7 mmol) in dimethyl sulfoxide (10 mL) was added methyl amine (2.5 mL, 5 mmol, 2M solution in tetrahydrofuran) and the reaction heated to 120° C. for 1 hr. Water was added and product extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give 1 g (85%) of 3-(4-methoxybenzyl)6-fluoro-7-(methylamino)2,3-dihydrobenzo[e][1,3]oxazin-4-one. RP-HPLC: 2.82 min; ES-MS (M+H)+=318.0; 1H-NMR (DMSO-d6) δ (ppm): 7.6 (d, 1), 6.8 (d, 2), 6.4 (d, 1H), 5.0 (s, 2), 4.6 (s, 2), 3.7 (s, 3), 2.8 (s, 3).

Workup

  1. extractionproduct extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59a46994645a4c6f92b1816dd0958d8f
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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