Oxalyl chloride → Tert-butyl 2-(4-fluorobenzyl)-2-[(8-benzyloxy-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)carbonyl]hydrazinecarboxylate

HRID 494108Notes

Reaction equation

HRID 494108 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH2:27]([O:34][C:35]1[C:36]([C:46](Cl)=[O:47])=[CH:37][N:38]2[CH2:43][CH2:42][N:41]([CH3:44])[C:40](=[O:45])[C:39]=12)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(Cl)(=O)C(Cl)=O>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]([C:46]([C:36]2[C:35]([O:34][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:39]3[C:40](=[O:45])[N:41]([CH3:44])[CH2:42][CH2:43][N:38]3[CH:37]=2)=[O:47])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 10705205Tert-butyl 2-(4-fluorobenzyl)hydrazinecarboxylateHCID 876068658-(Benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carbonyl chloride

Product 1

HCID 68864457Tert-butyl 2-(4-fluorobenzyl)-2-[(8-benzyloxy-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)carbonyl]hydrazinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a cold (0° C.) solution of tert-butyl 2-(4-fluorobenzyl)hydrazinecarboxylate (7.30 g, 30.37 mmol; see Fassler et al., J. Med Chem. 1996, 3203) and diisopropylethylamine (10.70 g, 82.82 mmol) in dichloromethane (200 mL), a solution of 8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carbonyl chloride (8.80 g, 27.61 mmol; derived from treatment of the corresponding acid with oxalyl chloride in dichloromethane in the presence of catalytic amount of DMF at room temperature) in dichloromethane was added. The resultant mixture was stirred at room temperature overnight. The resultant mixture was washed with aqueous ammonium chloride, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the titled amide. This was used with no further purification.

Workup

  1. additionwas added
  2. washThe resultant mixture was washed with aqueous ammonium chloride, and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f7f4a351a8fd449aba3d21f9e63ddbb9
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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