Cyclopentylmethyl 4-methylbenzene-1-sulfonate → HCID 57744448, compound

HRID 1887321Notes

Reaction equation

HRID 1887321 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.[CH2:18]([NH:25][C:26]([C:28]1[S:32][C:31]([N:33]2[CH:38]=[CH:37][C:36](O)=[CH:35][C:34]2=[O:40])=[N:30][C:29]=1[CH3:41])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][C:26]([C:28]1[S:32][C:31]([N:33]2[CH:38]=[CH:37][C:36]([O:11][CH2:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[CH:35][C:34]2=[O:40])=[N:30][C:29]=1[CH3:41])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744448HCID 57744448, compoundYield 57%

Procedure

Following the procedure as described in Example 9, making variation only as required to use cyclopentylmethyl 4-methylbenzenesulfonate 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 57% yield: mp 196-198° C. (methanol); 1H NMR (300 MHz, CDCl3) δ 8.64 (d, J=8.1 Hz, 1H), 7.40-7.25 (m, 5H), 6.16 (d, J=8.1, 2.6 Hz, 1H), 6.09-6.05 (m, 1H), 5.94 (d, J=2.6 Hz, 1H), 4.58 (d, J=5.6 Hz, 2H), 3.83 (d, J=7.0 Hz, 2H), 2.68 (s, 3H) 2.41-2.27 (m, 1H), 1.87-1.77 (m, 4H), 1.66-1.58 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 167.9, 162.2, 162.1, 153.6, 152.2, 137.7, 131.3, 128.8, 127.9, 127.7, 122.1, 104.2, 96.6, 73.3, 44.1, 38.4, 29.3, 25.3, 17.3; MS (ES+) m/z 424.3 (M+1).

Sources & evidence

ORD record
ord-b81eae96eb684bef95b46eb04a981bbe
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…