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

HRID 32904Notes

Reaction equation

[Cl: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>>[Cl: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 9523943-Chloro-2-piperidin-1-yl-phenylamine

HCID 202590395-Cyano-2-furoyl chloride

Product 1

HCID 116096145-Cyano-furan-2-carboxylic Acid (3-chloro-2-piperidin-1-yl-phenyl)-amideYield 10%

Procedure

Using a procedure similar to Example 3, step (d), 3-chloro-2-piperidin-1-yl-phenylamine (54 mg, 0.25 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (55.8 mg, 0.360 mmol) in the presence of DIEA (95 μL, 0.55 mmol) to afford 8.4 mg (10%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 10.70 (br s, 1H), 8.42 (dd, 1H, J=1.4, 8.1 Hz), 7.30 (dd, J=1.5, 3.7 Hz), 7.24 (d, 1H, J=3.7 Hz), 7.17 (t, 1H, J=8.1 Hz), 7.07 (dd, 1H, J=1.4, 8.1 Hz), 3.58-3.52 (m, 2H), 2.85-2.82 (m, 2H), 2.02-1.99 (m, 1H), 1.89-1.72 (m, 4H), 1.52-1.38 (m, 1H), Mass spectrum (ESI, m/z): Calcd. for C17H16ClN3O2, 330.0 (M+H), found 330.1.

Workup

customas prepared in the previous step)

Sources & evidence

ORD record: ord-daabe9bbf62f431c9b7209890782dd76
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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