Acetoxyacetyl chloride → acetic acid [4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-ylcarbamoyl]-methyl ester

HRID 1663174Notes

Reaction equation

HRID 1663174 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[O:11][C:10]2=[O:20])[CH:5]=[CH:4][N:3]=1.[C:21]([O:24][CH2:25][C:26](Cl)=[O:27])(=[O:23])[CH3:22]>N1C=CC=CC=1>[O:20]=[C:10]1[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:26]([CH2:25][O:24][C:21](=[O:23])[CH3:22])=[O:27])[CH:7]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[O:11]1

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 583773961-(2-Amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 86615650acetic acid [4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-ylcarbamoyl]-methyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-(2-amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione (600 mg, see preparation 7b) in pyridine (5 ml) was added acetoxyacetyl chloride (0.29 ml). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure. The remaining oil was dissolved in EtOAc and washed with water and brine. The organic layer was concentrated to ca. 10 ml under reduced pressure. The resulting solid material was isolated by filtration and dried in vacuo, affording acetic acid [4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-ylcarbamoyl]-methyl ester.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe remaining oil was dissolved in EtOAc
  3. washwashed with water and brine
  4. concentrationThe organic layer was concentrated to ca. 10 ml under reduced pressure
  5. customThe resulting solid material was isolated by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6e5ddfe2ca5d4686b3d3c1147efa3e26
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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