Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate → 4-Methyl-2-(2-oxo-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

HRID 554895Notes

Reaction equation

HRID 554895 reaction equation
FC1C=C[C:5]([CH2:6][NH:7][C:8](=[O:27])[CH2:9][N:10]2[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=3)[C:11]2=[O:26])=[CH:4][CH:3]=1.CC1N=C(N2CCN(CC(=O)N3CCCC3)C2=O)SC=1C(OCC)=O>>[CH3:20][C:18]1[N:19]=[C:15]([N:12]2[CH2:13][CH2:14][N:10]([CH2:9][C:8](=[O:27])[N:7]3[CH2:3][CH2:4][CH2:5][CH2:6]3)[C:11]2=[O:26])[S:16][C:17]=1[C:21]([OH:23])=[O:22]

Participants

3

Reactant 2

HCID 57919793Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 57919832Ethyl 4-methyl-2-(2-oxo-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 579199084-Methyl-2-(2-oxo-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazolidin-1-yl)thiazole-5-carboxylic acidYield 85%

Procedure

Following the procedure as described in Preparation 9, making variations as required to replace ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with ethyl 4-methyl-2-(2-oxo-3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazolidin-1-yl)thiazole-5-carboxylate, the crude title compound was obtained as a colorless solid in 85% yield: 1H NMR (300 MHz, DMSO-d6) δ 12.84 (br s, 1H), 4.09-4.00 (m, 4H), 3.84 (s, 2H), 3.65-3.57 (m, 2H), 3.42 (t, J=6.7 Hz, 2H), 3.30 (t, J=6.7 Hz, 2H), 2.51 (s, 3H), 1.95-1.84 (m, 2H), 1.83-1.71 (m, 2H); MS (ES+) m/z 339.3 (M+1).

Workup

  1. customas described in Preparation 9

Sources & evidence

ORD record
ord-7f2c42de710245a4994578722b2483a8
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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