2-Pyrazinecarboxylic acid → HCID 59595989, compound

HRID 2264212Notes

Reaction equation

HRID 2264212 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.[F:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][C:38]=1[C:39]1[C:40]([C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)=[N:41][C:42]([NH2:46])=[C:43]([NH2:45])[CH:44]=1>CN(C=O)C>[NH2:46][C:42]1[N:41]=[C:40]([C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)[C:39]([C:38]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[F:32])=[CH:44][C:43]=1[NH:45][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine2×

Product 1

HCID 59595989HCID 59595989, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of pyrazine-2-carboxylic acid (0.114 g, 0.924 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.178 g, 0.924 mmol) and 1H-1,2,3-benzotriazol-1-ol (0.096 g, 0.712 mmol) in DMF (6 mL) was heated at 40° C. for 15 minutes. Finally, 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.1 g, 0.356 mmol) in DMF (1 mL) was added and the mixture was stirred at room temperature overnight. The crude mixture was extracted between ethyl acetate and water. The organic layer was washed with 4% sodium bicarbonate aqueous solution and water, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (90:10 dichloromethane/methanol) to give the title compound (0.057 g, 41% of yield).

Workup

  1. extractionThe crude mixture was extracted between ethyl acetate and water
  2. washThe organic layer was washed with 4% sodium bicarbonate aqueous solution and water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by silica gel flash chromatography (90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1eec0be91ed24db1b6b662b046a3550a
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

Loading…