2-Aminoisonicotinonitrile → 3-((2-(Methylthio)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-a]pyridine-7-carbonitrile

HRID 1848114Notes

Reaction equation

HRID 1848114 reaction equation
Cl[CH:2]([CH2:5][C:6]1[CH:16]=[CH:15][C:9]2[N:10]=[C:11]([S:13][CH3:14])[S:12][C:8]=2[CH:7]=1)[CH:3]=O.[NH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][N:25]=1)[C:21]#[N:22]>C(O)CCC>[CH3:14][S:13][C:11]1[S:12][C:8]2[CH:7]=[C:6]([CH2:5][C:2]3[N:25]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]4=[N:17][CH:3]=3)[CH:16]=[CH:15][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 70155242-AminoisonicotinonitrileHCID 866810872-Chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal

Product 1

HCID 866810883-((2-(Methylthio)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-a]pyridine-7-carbonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal (0.35 g, 1.3 mmol) and 2-aminoisonicotinonitrile (0.30 g, 2.6 mmol) in 1-butanol (15 mL) was heated at reflux overnight. After cooling to rt, the formed solid was collected and washed with water, then dried to afford 3-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-a]pyridine-7-carbonitrile as a white solid (0.27 g, 62%). 1H NMR (300 MHz, CDCl3) δ 8.45 (d, J=7.2 Hz, 1H), 8.34 (s, 1H), 7.90 (s, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.75 (s, 1H), 7.37 (dd, J=1.2, 7.8 Hz, 1H), 7.20 (dd, J=1.8, 7.2 Hz, 1H), 4.49 (s, 2H), 2.77 (s, 3H). LCMS (ESI) m/z 337 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe formed solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e5eb2fa8966344e9a93fdf3ae7ddff2c
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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