Diisopropylethylamine → HCID 11508605, compound

HRID 32915Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[C:18]([C:20]1[O:24][C:23]([C:25](Cl)=[O:26])=[CH:22][CH:21]=1)#[N:19].CCN(C(C)C)C(C)C>>[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:25]([C:23]2[O:24][C:20]([C:18]#[N:19])=[CH:21][CH:22]=2)=[O:26])=[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1)(=[O:11])[CH3:10]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 69310437HCID 69310437, compound

Product 1

HCID 11508605HCID 11508605, compoundYield 38%

Procedure

Using a procedure similar to Example 3, step (d), N-(4-amino-3-piperidin-1-yl-phenyl)-acetamide (40 mg, 0.17 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (27 mg, 0.17 mmol) in the presence of DIEA (65 μL, 0.37 mmol) to afford 23 mg (38%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.64 (s, 1H),), 8.36 (d, 1H, J=8.5 Hz), 7.70 (br s, 1H), 7.27 (br s, 1H), 7.22 (d, 1H, J=3.8 Hz), 7.14 (br s, 1H), 7.02 (dd, 1H, J=6.6, 8.9 Hz), 2.85 (br s, 4H), 2.18 (s, 3H), 1.80 (br s, 4H), 1.65 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C19H20N4O3, 353.1 (M+H), found 353.2.

Workup

customas prepared in the previous step)

Sources & evidence

ORD record: ord-05031f19a8fb4357880db6941b9a1220
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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