Ethyl 5-(3-(4-cyanobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate → 5-(3-(4-Carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

HRID 2067656Notes

Reaction equation

HRID 2067656 reaction equation
CC1C=C(N2CCN(CC[O:14]C3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[C:27]([C:29]1[CH:52]=[CH:51][C:32]([CH2:33][N:34]2[CH2:38][CH2:37][N:36]([C:39]3[S:43][C:42]([C:44]([O:46]CC)=[O:45])=[C:41]([CH3:49])[CH:40]=3)[C:35]2=[O:50])=[CH:31][CH:30]=1)#[N:28]>>[C:27]([C:29]1[CH:30]=[CH:31][C:32]([CH2:33][N:34]2[CH2:38][CH2:37][N:36]([C:39]3[S:43][C:42]([C:44]([OH:46])=[O:45])=[C:41]([CH3:49])[CH:40]=3)[C:35]2=[O:50])=[CH:51][CH:52]=1)(=[O:14])[NH2:28]

Participants

3

Reactant 2

HCID 58031419Ethyl 5-(3-(4-cyanobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateHCID 58031558Ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 580316105-(3-(4-Carbamoylbenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidYield 77%

Procedure

Following the procedure as described in Example 54, making variations as required to replace ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)-thiophene-2-carboxylate with ethyl 5-(3-(4-cyanobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate, the title compound was obtained as a colorless solid in 77% yield: 1H NMR (300 MHz, DMSO-d6) δ 7.97 (br s, 1H), 7.87 (d, J=7.9 Hz, 2H), 7.36 (d, J=7.9 Hz, 2H), 6.30 (s, 1H), 4.45 (s, 2H), 3.90-3.80 (m, 2H), 3.54-3.42 (m, 4H), 2.40 (s, 3H); MS (ES+) m/z 382.3 (M+23).

Sources & evidence

ORD record
ord-9577aee22b754b77be219f479457e2ed
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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