Oxalyl chloride → HCID 86617820, compound

HRID 1453851Notes

Reaction equation

HRID 1453851 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][N:12]2[CH:17]([C:18](O)=[O:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:31])=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:11][N:12]2[CH:17]([C:18]([Cl:31])=[O:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 68954581HCID 68954581, compound

Product 1

HCID 86617820HCID 86617820, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-benzyloxy-2-ethoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-7-carboxylic acid (250 mg, 0.670 mmol) in anhydrous CH2Cl2 at 0° C. were added 2M oxalyl chloride in CH2Cl2 (1.339 mL, 2.678 mmol) and DMF (1 drop). The reaction was stirred at 0° C. for 30 minutes and allowed to warm to room temperature for 1 hour. The mixture was concentrated in vacuo and azeotroped twice with anhydrous CH2Cl2 to afford the title product. ES MS (M+H)=392.

Workup

  1. temperatureto warm to room temperature for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. customazeotroped twice with anhydrous CH2Cl2

Sources & evidence

ORD record
ord-3ac61e66cc5d429a955f7c5826e80e28
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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