Triethylamine → HCID 178499186, compound

HRID 2173720Notes

Reaction equation

HRID 2173720 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=O)=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.CCN(CC)CC.[NH2:23][C:24]1[NH:28][N:27]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[N:25]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCOC(C)=O.CCCC(C)C>C(Cl)Cl.CC#N.O>[NH2:1][C:2]1[C:3]([C:13]([NH:23][C:24]2[NH:28][N:27]=[C:26]([C:29]([O:31][CH3:32])=[O:30])[N:25]=2)=[O:15])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:9])([F:10])[F:11])[N:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 2724699PyBOPHCID 21882781Isohexane ethyl acetateHCID 58442296HCID 58442296, compound2×HCID 178499187HCID 178499187, compound

Product 1

HCID 178499186HCID 178499186, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (300 mg, 1.049 mmol) in dry DCM (10 ml) was added NEt3 (0.322 ml, 2.308 mmol) followed by methyl 5-amino-1H-1,2,4-triazole-3-carboxylate (149 mg, 1.049 mmol). After stirring at RT for 5 minutes the reaction mixture was treated with PyBOP (546 mg, 1.049 mmol) and stirred for 3 hours. The mixture was partitioned between DCM (20 ml) and water (20 ml), shaken and separated. The organic portion was washed with water (20 ml), dried over MgSO4, filtered and concentrated in vacuo to give an orange oil. Purification of the crude residue by chromatography on silica eluting with 0-100% EtOAc in iso-hexane, followed by 0-35% MeOH in EtOAc afforded a yellow oil. Trituration of the oil with EtOAc/iso-hexane followed by MeCN/water afforded the title compound as a yellow solid.

Workup

  1. stirringstirred for 3 hours
  2. customThe mixture was partitioned between DCM (20 ml) and water (20 ml)
  3. stirringshaken
  4. customseparated
  5. washThe organic portion was washed with water (20 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil
  10. customPurification of the crude residue by chromatography on silica eluting with 0-100% EtOAc in iso-hexane
  11. customafforded a yellow oil

Sources & evidence

ORD record
ord-b4eb6f5f58d14092883b444fd63d1ebb
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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