Diisopropylethylamine → HCID 11718404, compound

HRID 1445183Notes

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][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([C:25]3[C:29]([CH3:30])=[CH:28][S:27][CH:26]=3)[CH:19]=2)[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:8]([C:6]3[O:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[O:9])=[C:20]([C:25]3[C:29]([CH3:30])=[CH:28][S:27][CH:26]=3)[CH:19]=2)[CH2:14][CH2:13]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 59463820HCID 59463820, compound

Product 1

HCID 11718404HCID 11718404, compoundYield 24%

Procedure

Using a procedure similar to Example 9, step (c), 5-cyano-furan-2-carbonyl chloride (64 mg, 0.41 mmol, as prepared in Example 9, step (c)) was allowed to react with 4-(4-methyl-piperazin-1-yl)-2-(4-methyl-thiophen-3-yl)-phenylamine (80 mg, 0.27 mmol, as prepared in the previous step) in the presence of DIEA (0.10 mL, 0.59 mmol) to afford 25.8 mg (24%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 2.09 (s, 3H), 2.37 (s, 3H), 2.59-2.60 (m, 4H), 3.24-3.26 (m, 4H), 6.83 (d, 1H, J=2.9 Hz), 6.98-7.06 (m, 2H), 7.14-7.21 (m, 3H), 7.96 (s, 1H), 8.32 (d, 1H, J=9.0 Hz). Mass spectrum (ESI, m/z): Calcd. for C22H22N4O2S, 407.1 (M+H), found 407.1.

Sources & evidence

ORD record: ord-125df3ba50f548c08936978ca1122e24
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662837B2

Reaction notes

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