Dimethylformamide → HCID 68567079, compound

HRID 2100500Notes

Reaction equation

HRID 2100500 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:11]([N:14]([CH:17](C)C)CC)(C)[CH3:12].[N:20]1(OC(N(C)C)=[N+](C)C)[C:24]2[N:25]=CC=CC=2N=N1.CN(C=[O:41])C>>[N:14]1([CH2:11][C:12]([NH:1][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])=[O:41])[CH:17]=[N:25][CH:24]=[N:20]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 5066232-Aminopyridine-3-carboxamideHCID 4641409(Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminium

Product 1

HCID 68567079HCID 68567079, compound

Procedure

To a solution of 2-amino-nicotinamide (200 mg, 1.4 mmol) in DMF (3 ml) was added successively 1H-1,2,4-triaazole-1-acetic acid [28711-29-7] (185 mg, 1.4 mmol), diisopropylethylamine [7087-68-5] (200 μl, 1.4 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphatehexafluorophosphate [200731-31-3] (555 mg, 1.4 mmol) at r.t. The reaction mixture was stirred for 18 hours. The solvent was removed in vacuo, and the residue was digested with dichloromethane to yield product as an off-white solid. Filtration and drying gave 206 mg of 2-(2-[1,2,4]triazol-1-yl-acetylamino)-nicotinamide as off-white solid, which was used without further purification in the next step.

Workup

  1. customat r.t
  2. customThe solvent was removed in vacuo
  3. customto yield product as an off-white solid
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-c9031a93f6884c50a19d32de6405797e
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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