Methyl iodide → HCID 24986111, compound

HRID 1887331Notes

Reaction equation

[CH3:1]I.[OH:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)[C:6](=[O:21])[CH:5]=1>>[CH3:1][O:3][C:4]1[CH:9]=[CH:8][N:7]([C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)[C:6](=[O:21])[CH:5]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 54742342HCID 54742342, compound

Product 1

HCID 24986111HCID 24986111, compoundYield 54%

Procedure

Following the procedure as described in Example 15, making variations only as required to use methyl iodide 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 yellowish solid in 54% yield: mp 163-165° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=8.1 Hz, 1H), 6.16 (dd, J=8.1, 2.7 Hz, 1H), 6.00 (d, J=2.7 Hz, 1H), 4.32 (q, J=7.1 Hz, 2H), 3.83 (s, 3H), 2.68 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 168.3, 162.9, 162.2, 156.6, 155.7, 131.3, 119.7, 103.8, 96.3, 60.9, 56.0, 17.3, 14.3; MS (ES+) m/z 295.2 (M+1).

Sources & evidence

ORD record: ord-bda8a329d9ea40cd863c371d4b1f3841
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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