Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate → 2-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylic acid

HRID 560789Notes

Reaction equation

HRID 560789 reaction equation
C(NC(C1SC(N2CCN(CC3C=C(C=CC=3)C(OCC)=O)C2=O)=NC=1C)=O)C1C=CC=CC=1.[CH:35]1([CH2:38][N:39]2[CH2:43][CH2:42][N:41]([C:44]3[S:45][C:46]([C:49]([O:51]C)=[O:50])=[CH:47][N:48]=3)[C:40]2=[O:53])[CH2:37][CH2:36]1>>[CH:35]1([CH2:38][N:39]2[CH2:43][CH2:42][N:41]([C:44]3[S:45][C:46]([C:49]([OH:51])=[O:50])=[CH:47][N:48]=3)[C:40]2=[O:53])[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 58031461Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylateHCID 59481231Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

Product 1

HCID 580314172-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylic acidYield 93%

Procedure

Following the procedure as described in Example 25, making variations as required to replace ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate with methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in 93% yield: mp 250-252 (water); 1H NMR (300 MHz, DMSO-d6) δ 12.97 (s, 1H), 7.93 (s, 1H), 4.03-3.96 (m, 2H), 3.66-3.61 (m, 2H), 3.08 (d, J=7.1 Hz, 2H), 0.96-0.87 (m, 1H), 0.49-0.43 (m, 2H), 0.21-0.16 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 163.3, 162.8, 155.0, 145.2, 122.4, 48.2, 42.5, 42.4, 9.27, 3.62; MS (ES+) m/z 268.2 (M+1).

Sources & evidence

ORD record
ord-8ad6ded0f1d64475a771fc855116df03
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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