Isonicotinic Acid → HCID 21275762, compound

HRID 1628208Notes

Reaction equation

HRID 1628208 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.[NH2:11][CH2:12][C:13]#[N:14].O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)C(C)C)C.ClCCl>>[C:12]([CH2:13][NH:14][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)#[N:11]

Participants

7

Reactant 6

HCID 5922Isonicotinic AcidHCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 21275762HCID 21275762, compound

Procedure

A mixture of isonicotinic acid (1.00 g, 8.12 mmol), 2-aminoacetonitrile hydrochloride (0.902 g, 9.75 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (1.24 g, 8.12 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.71 g, 8.94 mmol) and N-ethyl-N-isopropylpropan-2-amine (4.95 ml, 28.4 mmol) in dichloromethane (20.3 ml, 8.12 mmol) was allowed to stir at room temperature for 24 hours. The mixture was concentrated and the residue was purified by CombiFlash using 0-10% methanol/DCM as the eluent to 1.31 g of N-(cyanomethyl)isonicotinamide 5.3B. 400 MHz 1H NMR (CDCl3) δ: 9.62 (br s, 1H), 8.87 (d, J=8.0 Hz, 2H), 7.94 (d, J=8.0 Hz, 2H), 4.30 (d, J=2H). LCMS (ES+) m/z 162.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-3bca1b638f9f449ab17f93632568c787
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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