Diisopropylethylamine → 5-Cyano-furan-2-carboxylic Acid (3-methyl-2-piperidin-1-yl-phenyl)-amide

Reaction equation

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

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693077873-Methyl-2-(1-piperidinyl)aniline

Product 1

HCID 117022975-Cyano-furan-2-carboxylic Acid (3-methyl-2-piperidin-1-yl-phenyl)-amideYield 12%

Procedure

Using a procedure similar to example 3, step (d), 3-methyl-2-piperidin-1-yl-phenylamine (68 mg, 0.35 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (65 mg, 0.42 mmol) in the presence of DIEA (134 μL, 0.77 mmol) to afford 13 mg (12%) of the title compound as a waxy yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 10.7 (br s, 1H), 8.33 (d, 1H, J=8.0 Hz), 7.27 (d, 1H, J=3.7 Hz), 7.22 (dd, 1H, 3.7 Hz), 7.12 (t, 1H, J=7.9 Hz), 6.87 (dd, 1H, J=0.7, 7.7 Hz), 3.22-3.28 (m, 2H), 2.88-2.91 (m, 1H), 2.41 (s, 3H), 2.01-2.04 (m, 1H), 1.80-1.86 (m, 4H), 1.43-1.47 (m, 1H); Mass spectrum (ESI, m/z): Calcd. for C18H19N3O2, 310.1 (M+H), found 310.2.