Diisopropylethylamine → 3-[(4-Cyanobenzyl)amino]pyridine-4-carboxylic acid

HRID 63036

Reaction equation

HRID 63036 reaction equation
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[NH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:13]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:15]=1)#[N:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 99422504-(Aminomethyl)benzonitrile hydrochloride

Product 1

HCID 867281953-[(4-Cyanobenzyl)amino]pyridine-4-carboxylic acidYield 18%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
166 °C

Procedure

3-Fluoroisonicotinic acid (100 mg, 0.71 mmol), 4-(aminomethyl)-benzonitrile hydrochloride (240 mg, 1.42 mmol), and DIEA (250 μL, 1.42 mmol) were combined in DMA (2 mL) and the reaction mixture was stirred at 166° C. in a microwave for 90 min. The solution was concentrated in vacuo and purified by silica gel chromatography (10-20% MeOH/DCM). The semi-pure fractions were concentrated and then taken up in water to give a pale yellow precipitate, which was collected by filtration and dried under vacuum to give 32 mg (18%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.10 (br s, 1H), 8.04 (s, 1H), 7.83 (d, 1H, J=5.0 Hz), 7.81 (d, 2H, J=8.0 Hz), 7.58 (d, 1H, J=5.0 Hz), 7.54 (d, 2H, J=8.0 Hz), 4.69 (s, 2H). [M+H] calc'd for C14H11N3O2, 254. found 254.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (10-20% MeOH/DCM)
  3. concentrationThe semi-pure fractions were concentrated
  4. customto give a pale yellow precipitate, which
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0d745710e5544d009a976982d437d216
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Linked notes

Loading…