Diisopropylethylamine → N-(4-(1H-imidazol-1-yl)-2-(piperidin-1-yl)phenyl)-5-cyanofuran-2-carboxamide

HRID 32892Notes

Reaction equation

[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:19]([C:21]1[O:25][C:24]([C:26](Cl)=[O:27])=[CH:23][CH:22]=1)#[N:20].CCN(C(C)C)C(C)C>>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:26]([C:24]3[O:25][C:21]([C:19]#[N:20])=[CH:22][CH:23]=3)=[O:27])=[C:8]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693102344-Imidazol-1-yl-2-piperidin-1-yl-phenylamine

Product 1

HCID 11574080N-(4-(1H-imidazol-1-yl)-2-(piperidin-1-yl)phenyl)-5-cyanofuran-2-carboxamideYield 44%

Procedure

Using a procedure similar to Example 3, step (d), 4-imidazol-1-yl-2-piperidin-1-yl-phenylamine (69 mg, 0.28 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (56 mg, 0.36 mmol) in the presence of DIEA (138 μL, 0.790 mmol) to afford 44.9 mg (44%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.65 (br s, 1H), 8.57 (d, 1H, J=9.3 Hz), 7.84 (s, 1H), 7.34 (d, 1H, J=3.7 Hz), 7.28-7.27 (m, 2H), 7.22-7.20 (m, 3H), 2.93-2.90 (m, 4H), 1.88-1.85 (m, 4H), 1.72 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C20H19N5O2, 362.1 (M+H), found 362.2.

Workup

customas prepared in the previous step)

Sources & evidence

ORD record: ord-946a82ee713e43c98d5c91fb68b998b4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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