Furan, 2-(bromomethyl)tetrahydro- → HCID 57744449, compound

HRID 1887323Notes

Reaction equation

HRID 1887323 reaction equation
Br[CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][O:4]1.[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([N:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]2=[O:30])=[N:20][C:19]=1[CH3:31])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([N:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:2][CH:3]3[CH2:7][CH2:6][CH2:5][O:4]3)=[CH:25][C:24]2=[O:30])=[N:20][C:19]=1[CH3:31])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744449HCID 57744449, compoundYield 42%

Procedure

Following the procedure as described in Example 9, making variation only as required to use 2-(bromomethyl)tetrahydrofuran in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 42% yield: mp 181-183° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.66-8.62 (m, 1H), 7.38-7.26 (m, 5H), 6.22-6.18 (m, 1H), 6.14-6.12 (m, 1H), 5.95-5.94 (m, 1H), 4.58-4.54 (m, 2H), 4.33-4.20 (m, 1H), 3.99-3.78 (m, 4H), 2.67 (s, 3H), 2.13-1.90 (m, 3H), 1.77-1.66 (m, 1H); MS (ES+) m/z 426.3 (M+1), 448.3 (M+23).

Sources & evidence

ORD record
ord-ba77b9500f864d9d8248e0a35dbb3616
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…