Acetic-formic anhydride → HCID 58447022, compound

HRID 1045760Notes

Reaction equation

HRID 1045760 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:5][CH:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.[CH:27](OC(=O)C)=[O:28]>ClCCl>[CH:27]([NH:1][CH2:2][C:3]1[C:4]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:5][CH:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=[O:28]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 58447012HCID 58447012, compound

Product 1

HCID 58447022HCID 58447022, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottom flask was charged with tert-butyl 4-(3-(aminomethyl)-5-(thiophen-2-yl)pyrazin-2-yl)piperazine-1-carboxylate (0.70 g, 1.86 mmol), acetic formic anhydride (270 mg, 3.72 mmol) and dichloromethane (20 mL). The resulting mixture was stirred at room temperature overnight. Work-up: the reaction mixture was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 50% EtOAc in petroleum ether, to afford 490 mg (65%) of the product.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel with 50% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-bb8f1ceb76714f3285a8c7603f485957
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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