Cyclopropylboronic acid → HCID 57744441, compound

HRID 1887336Notes

Reaction equation

[CH:1]1(B(O)O)[CH2:3][CH2:2]1.FC(F)(F)S(O[C:13]1[CH:18]=[CH:17][N:16]([C:19]2[S:20][C:21]([C:25](=[O:34])[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:22]([CH3:24])[N:23]=2)[C:15](=[O:35])[CH:14]=1)(=O)=O>>[CH2:27]([NH:26][C:25]([C:21]1[S:20][C:19]([N:16]2[CH:17]=[CH:18][C:13]([CH:1]3[CH2:3][CH2:2]3)=[CH:14][C:15]2=[O:35])=[N:23][C:22]=1[CH3:24])=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 2760897Cyclopropylboronic acid

HCID 24985792HCID 24985792, compound

Product 1

HCID 57744441HCID 57744441, compoundYield 54%

Procedure

Following the procedure as described in Example 19, making variations only as required to use cyclopropylboronic acid in place of phenethylboronic acid to react with -(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate, the title compound was obtained as a colorless solid in 54% yield: mp 149-151° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.63 (d, J=7.6 Hz, 1H), 7.39-7.25 (m, 5H), 6.39 (d, J=1.5 Hz, 1H), 6.10-6.05 (m, 2H), 4.58 (d, J=5.6 Hz, 2H), 2.69 (s, 3H), 1.81-1.72 (m, 1H), 1.14-1.07 (m, 2H), 0.86-0.81 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.2, 160.3, 158.8, 153.4, 152.3, 137.7, 130.3, 128.8, 127.9, 127.6, 127.7, 114.7, 106.6, 44.1, 17.3, 15.4, 10.4; MS (ES+) m/z 366.1 (M+1).

Sources & evidence

ORD record: ord-aff7bc047c3147948ee4c7abd7eaf10a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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