Diisopropylethylamine → HCID 11551574, compound

HRID 32889Notes

Reaction equation

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

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693077274-Methoxy-2-piperidin-1-yl-phenylamine

Product 1

HCID 11551574HCID 11551574, compoundYield 60%

Procedure

Using a procedure similar to Example 1, step (e), 5-cyano-furan-2-carbonyl chloride (66 mg, 0.43 mmol) was allowed to react with 4-methoxy-2-piperidin-1-yl-phenylamine (67 mg, 0.32 mmol, as prepared in the previous step) in the presence of DIEA (164 μL, 0.940 mmol) for 2 h to afford 62 mg (60%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.49 (br s, 1H) 8.35 (d, 1H, J=8.9 Hz), 7.27-7.22 (m, 1H), 6.76 (d, 1H, J=2.7 Hz), 6.71 (dd, 1H, J=2.8, 8.9 Hz), 3.81 (s, 3H), 2.85-2.83 (m, 4H), 1.84-1.78 (m, 4H), 1.66-1.65 (m, 2H); Mass spectrum (ESI, m/z): Calcd. for C18H19N3O3, 326.1 (M+H), found 326.1.

Sources & evidence

ORD record: ord-a5912ecb2806410cb5f96ce2cc6c0586
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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