Diisopropylethylamine → HCID 11659959, compound

HRID 32898Notes

Reaction equation

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

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 693077102-(4,4-Difluoropiperidin-1-yl)aniline

Product 1

HCID 11659959HCID 11659959, compoundYield 36.2%

Procedure

Using a procedure similar to Example 3, step (d), 2-(4,4-difluoro-piperidin-1-yl)-phenylamine (76 mg, 0.35 mmol) was allowed to react with 5-cyano-furan-2-carbonyl chloride (62 mg, 0.40 mmol) in the presence of DIEA (134 μL, 0.770 mmol) to afford 42 mg (36%) of the title compound as a tan solid. 1H-NMR (CDCl3; 400 MHz): δ 9.60 (br s, 1H), 8.44 (dd, 1H, J=1.3, 8.1 Hz) 7.32 (d, 1H, J=3.8 Hz), 7.27-7.21 (m, 3H), 7.18-7.13 (m, 1H), 3.07-3.04 (m, 4H), 2.29-2.21 (m, 4H); Mass spectrum (ESI, m/z): Calcd. for C17H15F2N3O2, 332.1 (M+H), found 332.1.

Sources & evidence

ORD record: ord-e16dafb3ea22421bb7655e5be6cfbb40
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Reaction notes

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