Toluene-4-sulfonic acid 2-cyclopropyl-ethyl ester → HCID 24986112, compound

HRID 1887332Notes

Reaction equation

HRID 1887332 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:3][CH2:2]1.O[C:18]1[CH:23]=[CH:22][N:21]([C:24]2[S:25][C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:27]([CH3:29])[N:28]=2)[C:20](=[O:35])[CH:19]=1>>[CH:1]1([CH2:4][CH2:5][O:6][C:18]2[CH:23]=[CH:22][N:21]([C:24]3[S:25][C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:27]([CH3:29])[N:28]=3)[C:20](=[O:35])[CH:19]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 54742342HCID 54742342, compound

Product 1

HCID 24986112HCID 24986112, compoundYield 35%

Procedure

Following the procedure as described in Example 15, making variations only as required to use 2-cyclopropylethyl-4-methylbenzenesulfonate in place of (bromomethyl)cyclopropane to react with ethyl 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colorless solid in 35% yield: mp 188-190° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.67 (dd, J=8.1, 1.1 Hz, 1H), 6.17-6.13 (m, 1H), 6.00-5.99 (m, 1H), 4.35-4.27 (m, 2H), 4.04 (t, J=6.6 Hz, 2H), 2.68 (s, 3H), 1.68 (q, J=6.6 Hz, 2H), 1.35 (dt, J=7.1, 1.3 Hz, 3H), 0.90-0.68 (m, 1H), 0.52-0.44 (m, 2H), 0.14-0.09 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 167.8, 162.9, 162.2, 156.6, 155.6, 131.3, 119.7, 104.1, 96.7, 69.1, 60.9, 33.6, 17.3, 14.3, 7.5, 4.2; MS (ES+) m/z 349.2 (M+1).

Sources & evidence

ORD record
ord-3bfa55bba0f3449397b8c790d4de77dc
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…