2-Pyrazinecarboxylic acid → HCID 178427876, compound

HRID 536667Notes

Reaction equation

HRID 536667 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](O)=O.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:39][C:40]1[C:61]([NH2:62])=[CH:60][C:43]2[CH2:44][C@@H:45]3[C:50]([CH3:52])([CH3:51])[C@:49]([CH3:53])([C:42]=2[CH:41]=1)[CH2:48][CH2:47][N:46]3[C:54](=[O:59])[C:55]([F:58])([F:57])[F:56]>CN(C)C=O.CCOC(C)=O>[F:58][C:55]([F:56])([F:57])[C:54]([N:46]1[CH2:47][CH2:48][C@:49]2([CH3:53])[C:50]([CH3:52])([CH3:51])[C@H:45]1[CH2:44][C:43]1[CH:60]=[C:61]3[N:62]=[C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)[NH:39][C:40]3=[CH:41][C:42]=12)=[O:59]

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58123670HCID 58123670, compound

Product 1

HCID 178427876HCID 178427876, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of pyrazine-2-carboxylic acid (152 mg), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (397 mg), and triethylamine (0.5 mL) in dimethylformamide (5 mL) is stirred at room temperature for 30 min, before 1-[(2R,6S)-8,9-diamino-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (300 mg) is added. The solution is stirred at room temperature overnight. Then, the solution is diluted with EtOAc and washed with water and 2 M aqueous K2CO3 solution and dried (MgSO4). The solvent is removed under reduced pressure and the residue is taken up in acetic acid (5 mL). The resulting solution is heated at 80° C. overnight. Then, the solvent is removed under reduced pressure and the residue is evaporated twice with toluene to give the crude title compound that is used without further purification.

Workup

  1. additionis added
  2. washwashed with water and 2 M aqueous K2CO3 solution
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed under reduced pressure
  5. temperatureThe resulting solution is heated at 80° C. overnight
  6. customThen, the solvent is removed under reduced pressure
  7. customthe residue is evaporated twice with toluene

Sources & evidence

ORD record
ord-571f256ad25144e2bebae9cf2eadb559
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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