Trimethylsilyldiazomethane → 5'-Amino-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4,6'-dicarboxylic acid 4-tert-butyl ester 6'-methyl ester

HRID 2242906Notes

Reaction equation

HRID 2242906 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][C:17]([NH2:20])=[C:16]([C:21]([OH:23])=[O:22])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[CH3:24][O:22][C:21]([C:16]1[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[CH:19]=[N:18][C:17]=1[NH2:20])=[O:23]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 667448533-Amino-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

Product 1

HCID 685422835'-Amino-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4,6'-dicarboxylic acid 4-tert-butyl ester 6'-methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 5′-amino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4,6′-dicarboxylic acid 4-tert-butyl ester (510 mg, 1.6 mmol; see Example 16 (e) above) in benzene (4 mL) and methanol (4 mL) was added a solution of trimethylsilyldiazomethane (2 M in hexane, 2 mL). The reaction was stirred at room temperature for overnight. The solvent was then removed in vacuo and the residue was purified by flash chromatography using ethyl acetate/hexanes (40:60) as eluant to afford 5′-amino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4,6′-dicarboxylic acid 4-tert-butyl ester 6′-methyl ester as a yellow solid (520 mg, 96%). 1H NMR (300 MHz, CDCl3) δ1.49 (s, 9H), 3.40 (s, 4H), 3.59 (s, 4H), 3.95 (s, 3H), 8.01 (s, 1 H); 13C NMR (100 MHz, CDCl3) δ 28.41, 46.30, 52.52, 80.05, 119.69, 135.58, 148.24, 150.00, 154.70, 167.10.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-94b6a118e07e4eeca2c49f2f2d652693
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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