Diisopropylethylamine → 5-cyano-N-(4-ethoxy-2-(piperidin-1-yl)phenyl)furan-2-carboxamide

HRID 32901Notes

Reaction equation

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

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693077324-Ethoxy-2-(piperidin-1-yl)aniline

Product 1

HCID 116957845-cyano-N-(4-ethoxy-2-(piperidin-1-yl)phenyl)furan-2-carboxamideYield 54%

Procedure

Using a procedure similar to Example 3, step (d), 4-ethoxy-2-piperidin-1-yl-phenylamine (64 mg, 0.29 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (66.6 mg, 0.430 mmol) in the presence of DIEA (111 μL, 0.63 mmol) to afford 53 mg (54%) of the title compound as a light yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 9.49 (br s, 1H), 8.32 (d, 1H, J=8.9 Hz), 7.25 (d, 1H, J=2.7 Hz), 7.22 (d, 1H, J=2.8 Hz), 6.77 (d, 1H, J=2.8 Hz), 6.67 (dd, 1H, J=2.8, 8.9 Hz), 2.82 (m, 4H), 4.02 (q, 2H, J=7.0 Hz), 2.82 (m, 4H), 1.80-1.82 (m, 4H), 1.64 (br s, 2H), 1.41 (t, 3H, J=7.0 Hz); Mass spectrum (ESI, m/z): Calcd. for C19H21N3O3, 340.1 (M+H), found 340.1.

Workup

customas prepared in the previous step)

Sources & evidence

ORD record: ord-f1ac5e3702ae44638c5c5c369e7972f8
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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