Diisopropylethylamine → HCID 11560584, compound

HRID 646885Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[O:10])=[CH:4][C:3]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[C:22]([C:24]1[O:28][C:27]([C:29](Cl)=[O:30])=[CH:26][CH:25]=1)#[N:23].CCN(C(C)C)C(C)C>>[C:22]([C:24]1[O:28][C:27]([C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[O:10])=[CH:4][C:3]=2[N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:30])=[CH:26][CH:25]=1)#[N:23]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 86241579HCID 86241579, compound

Product 1

HCID 11560584HCID 11560584, compoundYield 20%

Procedure

Using a procedure similar to Example 4, step (c), acetic acid (4-amino-3-piperidin-1-yl-phenylcarbamoyl)-methyl ester (80 mg, 0.27 mmol) was allowed to react with 5-cyano-furan-2-carbonyl chloride (42 mg, 0.27 mmol) in the presence of DIEA (0.10 mL, 0.59 mmol) to afford 22 mg (20%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.66 (s, 1H), 8.40 (d, 1H, J=9.0 Hz), 7.73-7.76 (m, 2H), 7.27-7.28 (m, 1H), 7.22 (d, 1H, J=2.7 Hz), 7.08 (dd, 1H, J=2.3, 8.7 Hz), 4.68 (s, 2H), 2.84-2.86 (m, 4H), 2.24 (s, 3H), 1.82-1.84 (m, 4H), 1.68 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C21H22N4O5, 411.1 (M+H), found 411.1.

Sources & evidence

ORD record: ord-5ce2a61931dd4dae8634d03057159d19
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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