2-Pyrazinecarboxylic acid → HCID 11677803, compound

HRID 1817845Notes

Reaction equation

HRID 1817845 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[N:28]1[CH:33]=[CH:32][N:31]=[CH:30][C:29]=1[C:34]([OH:36])=O.CCN(C(C)C)C(C)C.[CH:46]1([C:52]2[CH:53]=[CH:54][C:55]([O:72][CH3:73])=[C:56]([C:58]3[N:59]=[C:60]([NH:63][C:64]([CH:66]4[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]4)=[O:65])[S:61][CH:62]=3)[CH:57]=2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>C(#N)C>[CH:46]1([C:52]2[CH:53]=[CH:54][C:55]([O:72][CH3:73])=[C:56]([C:58]3[N:59]=[C:60]([NH:63][C:64]([CH:66]4[CH2:67][CH2:68][N:69]([C:34]([C:29]5[CH:30]=[N:31][CH:32]=[CH:33][N:28]=5)=[O:36])[CH2:70][CH2:71]4)=[O:65])[S:61][CH:62]=3)[CH:57]=2)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86616217HCID 86616217, compound

Product 1

HCID 11677803HCID 11677803, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.32 g of BOP, 0.08 g of pyrazinecarboxylic acid and then 0.37 mL of DIPEA are added, at a temperature of 0° C., to a solution of 0.25 g of the compound prepared in step 1.2 in 3 mL of acetonitrile. The medium is stirred at room temperature for 12 hours and then concentrated. The medium is taken up in EtOAc and washed 3 times with 10% Na2CO3 solution and then with saturated NaCl solution. After drying over MgSO4, the solution is concentrated and then purified by flash chromatography to give 0.23 g of a dark yellow solid.

Workup

  1. concentrationconcentrated
  2. washwashed 3 times with 10% Na2CO3 solution
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution is concentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8a3c02256573408b953219c401eb3d45
Source dataset
uspto-grants-2009_10
Patent number
US07598392B2

Reaction notes

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