Triethylamine → HCID 58114924, compound

HRID 2197483Notes

Reaction equation

HRID 2197483 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][C:10]([OH:12])=O)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][CH:20]=[CH:19][N:18]=1)=[O:16].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[CH3:13][O:14][C:15]([C:17]1[C:22]([NH:23][C:10](=[O:12])[CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=2)=[N:21][CH:20]=[CH:19][N:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 58114928HCID 58114928, compound

Product 1

HCID 58114924HCID 58114924, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-dichloro-pyrid-2-yl)-acetic acid (Example 5.1) (5.7 g) and 3-amino-pyrazine-2-carboxylic acid methyl ester (4.65 g) in dichloromethane (120 ml) were added successively triethylamine (8.5 ml) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (“BOP-Cl”) (7.5 g). The reaction mixture was stirred at ambient temperature for 24 hours. The organic phase was washed successively with water, aqueous sodium hydrogen carbonate (1M), and brine. The organic phase was dried over magnesium sulfate and concentrated to give 3-[2-(3,5-dichloro-pyrid-2-yl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester (6.37 g). 1H-NMR (400 MHz, CDCl3): 4.04 (s, 3H), 4.35 (s, 2H), 7.77 (s, 1H), 8.39 (s, 1H), 8.49 (s, 1H), 8.56 (s, 1H), 11.02 (s, 1H) ppm.

Workup

  1. washThe organic phase was washed successively with water, aqueous sodium hydrogen carbonate (1M), and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6faa2d7aced844eaa11315b75e1def09
Source dataset
uspto-grants-2012_12
Patent number
US08338598B2

Reaction notes

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