Ethyl 2-(3-(2-cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate → 2-(3-(2-Cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HRID 560595Notes

Reaction equation

HRID 560595 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19]C=3)[C:13]2=[O:23])[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].C1(CCN2CCN(C3SC(C(OCC)=O)=C(C)N=3)C2=O)CC1>>[CH:21]1([CH2:22][CH2:17][N:14]2[CH2:15][CH2:16][N:12]([C:4]3[S:5][C:6]([C:7]([OH:9])=[O:8])=[C:2]([CH3:1])[N:3]=3)[C:13]2=[O:23])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 58031391Ethyl 2-(3-(2-cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 594812172-(3-(2-Cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 88%

Procedure

Following the procedure as described in Example 6, making variations as required to replace ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate with ethyl 2-(3-(2-cyclopropylethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained in 88% yield: 1H NMR (300 MHz, DMSO-d6) δ 4.20-3.04 (m, 6H), 2.45 (s, 3H), 1.50-1.41 (m, 2H), 0.78-0.54 (m, 1H), 0.43-0.28 (m, 2H), 0.10-0.96 (m, 2H); MS (ES+) m/z 296.2 (M+1).

Sources & evidence

ORD record
ord-b2b27cbacea447f4b0f42c2a24af1b75
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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