Diisopropylethylamine → HCID 11573636, compound

HRID 32896

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]C)=[C:5]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1.[C:17]([C:19]1[O:23][C:22]([C:24](Cl)=[O:25])=[CH:21][CH:20]=1)#[N:18].[CH3:27]CN(C(C)C)C(C)C>>[CH3:1][N:2]([CH3:27])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:24]([C:22]2[O:23][C:19]([C:17]#[N:18])=[CH:20][CH:21]=2)=[O:25])=[C:5]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693103814-N,N-Dimethyl-2-piperidin-1-yl-benzene-1,4-diamine

Product 1

HCID 11573636HCID 11573636, compoundYield 63%

Procedure

Using a procedure similar to Example 3, step (d), 4-N,N-dimethyl-2-piperidin-1-yl-benzene-1,4-diamine (89 mg, 0.4 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (236 mg, 1.5 mmol) in the presence of DIEA (0.15 mL, 0.88 mmol) to afford 84.7 mg (63%) of the title compound as a yellow powder. 1H-NMR (CDCl3, 400 MHz): δ 9.50 (br s, 1H), 8.29 (d, 1H, J=8.9 Hz), 7.21-7.24 (m, 2H), 6.58 (d, 1H, J=2.7 Hz), 6.54 (dd, 1H, J=2.8, 9.0 Hz), 2.95 (s, 6H), 2.84-2.87 (m, 4H), 1.78-1.82 (m, 4H), 1.65 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C19H22N4O2, 339.1 (M+H), found 339.1.

Workup

customas prepared in the previous step)

Sources & evidence

ORD record: ord-7c0ab90fe07a46349c80d39c2a377cad
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Linked notes

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