2-Pyrazinecarboxylic acid → HCID 56340755, compound

HRID 1178091Notes

Reaction equation

HRID 1178091 reaction equation
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]([OH:18])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:41]=[C:42]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)[CH2:43][NH:44][C:45]([C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:49][CH:48]=1)=[O:46]>CN(C=O)C.O>[O:41]=[C:42]([N:59]1[CH2:64][CH2:63][N:62]([C:16]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][N:10]=2)=[O:18])[CH2:61][CH2:60]1)[CH2:43][NH:44][C:45]([C:47]1[CH:48]=[CH:49][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:51][CH:52]=1)=[O:46]

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 56340755HCID 56340755, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (149.8 mg, 1.15 mmol) was added to a stirred solution of pyrazine-2-carboxylic acid (31.9 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123.4 mg, 0.64 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.31 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, and the resulting precipitate was filtered. The residue was purified by column chromatography (using 60-120 mesh silica gel and 90% EtOAc in hexane as eluent) to afford 43 mg (38.9% yield) of biphenyl-4-carboxylicacid {2-oxo-2-[4-(pyrazine-2-carbonyl)-piperazin-1-yl]-ethyl}-amide, LC-MS purity: 86.93%, 1H NMR: (DMSO) δ 8.9 (s, 1H), 8.8 (s, 1H), 8.7 (q, 2H), 8.0 (d, 2H), 7.8-7.7 (q, 4H), 7.5 (t, 2H), 7.4 (t, 1H), 4.2 (dd, 2H), 3.8 (s, 1H), 3.7 (d, 3H), 3.6-3.5 (m, 4H).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe residue was purified by column chromatography (using 60-120 mesh silica gel and 90% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-8936eb9d74664e69ba711cbd27b95091
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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