Pyridine → HCID 61119065, compound

HRID 1628251Notes

Reaction equation

HRID 1628251 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[NH2:11][CH:12]([CH3:16])[C:13]([NH2:15])=O.N1C=CC=CC=1.Cl.C(N=C=NCCCN(C)C)C>>[C:13]([CH:12]([NH:11][C:5](=[O:7])[C:4]1[CH:3]=[CH:2][N:10]=[CH:9][CH:8]=1)[CH3:16])#[N:15]

Participants

5

Reactant 4

HCID 1049PyridineHCID 3502872-AminopropanamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628212-Methylpyridine-4-carboxylic acid

Product 1

HCID 61119065HCID 61119065, compoundYield 81.4%

Procedure

To a mixture of 2-methylisonicotinic acid (2.00 g, 15 mmol) and 2-aminopropanamide (3.7 g, 29 mmol) in pyridine (15 ml, 15 mmol) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (5.6 g, 29 mmol). The resulting mixture was allowed to stir at rt overnight. The mixture was concentrated, to the residue was added 10% methanol/DCM (80 mL). The white precipitate was collected and the residue was purified by CombiFlash using 0-10% methanol/DCM as the eluent to give 2.14 g of N-(1-cyanoethyl)isonicotinamide 22B. LCMS (ES+) m/z 208.

Workup

  1. concentrationThe mixture was concentrated, to the residue
  2. additionwas added 10% methanol/DCM (80 mL)
  3. customThe white precipitate was collected
  4. customthe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-5434f41c478c41118c75bc03166e6679
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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