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

HRID 1882391Notes

Reaction equation

HRID 1882391 reaction equation
F[C:2]1(F)[CH2:4][CH:3]1[CH2:5][N:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:17]([O:19]CC)=[O:18])=[C:14]([CH3:16])[N:15]=2)[C:7]1=[O:22].C(N1CCN(C2SC(C(OCC)=O)=C(C)N=2)C1=O)C(C)C>>[CH2:5]([N:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:17]([OH:19])=[O:18])=[C:14]([CH3:16])[N:15]=2)[C:7]1=[O:22])[CH:3]([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 57919846Ethyl 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 57919981Ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidYield 96%

Procedure

Following the procedure as described in Preparation 14, making variations as required to replace ethyl 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with ethyl 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colourless solid in 96% yield: 1H NMR (300 MHz, DMSO-d6) δ 4.04-3.98 (m, 2H), 3.58-3.53 (m, 2H), 3.03 (d, J=7.4 Hz, 2H), 2.50 (s, 3H), 1.94-1.85 (m, 1H), 0.87 (d, J=6.6 Hz, 6H); MS (ES+) m/z 283.8 (M+1).

Workup

  1. customas described in Preparation 14

Sources & evidence

ORD record
ord-ce5ba4c4bff745f2a5c9c82ebc279159
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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