Cyclopropanecarbonyl chloride → HCID 86615651, compound

HRID 1663176Notes

Reaction equation

HRID 1663176 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.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1>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:24]([CH:21]3[CH2:23][CH2:22]3)=[O:25])[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 77637Cyclopropanecarbonyl chlorideHCID 583773961-(2-Amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione

Product 1

HCID 86615651HCID 86615651, compound

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 (1.1 g, see preparation 7b) in pyridine (15 ml) was added cyclopropanecarbonyl chloride (512 mg). The reaction mixture was stirred at room temperature for 30 minutes, and 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 under reduced pressure and the resulting solid material was isolated by filtration and dried in vacuo, affording cyclopropanecarboxylic acid [4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-yl]-amide. Step 2: The above obtained anhydride intermediate was converted into the title compound by reaction with O-cyclopentyl-methylhydroxyl-amine hydrochloride (see preparation 66), using general procedure 1A. 13C-NMR (DMSO-d6) δ 172.4, 166.9, 152.3, 151.3, 148.5, 147.8, 132.4, 127.9, 117.3, 114.7, 113.3, 111.4, 111.3, 79.4, 45.4, 37.6, 28.9, 24.9, 14.1, 7.4.

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 under reduced pressure
  5. customthe resulting solid material was isolated by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ebe49bbfe0a3412b9a1a7ab27c242501
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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