3-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid → HCID 25097439, compound

HRID 560908Notes

Reaction equation

HRID 560908 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[F:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([OH:43])=O)=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.O.C(O)(=O)C(O)=O.C(O)(=O)C(O)=O.[CH3:61][C:62]1[C:66]([CH2:67][NH2:68])=[C:65]([CH3:69])[NH:64][N:63]=1>>[CH3:61][C:62]1[C:66]([CH2:67][NH:68][C:41]([C:39]2[S:40][C:36]([N:33]3[CH2:34][CH2:35][N:31]([CH2:30][C:29]4[CH:46]=[CH:47][C:26]([F:25])=[CH:27][CH:28]=4)[C:32]3=[O:45])=[CH:37][C:38]=2[CH3:44])=[O:43])=[C:65]([CH3:69])[NH:64][N:63]=1

Participants

4

Reactant 3

HCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidHCID 66631549HCID 66631549, compound

Product 1

HCID 25097439HCID 25097439, compoundYield 24%

Procedure

Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with (3,5-dimethyl-1H-pyrazol-4-yl)methanamine dioxalate monohydrate, the title compound was obtained as a colorless solid in 24% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.99 (m, 2H), 6.08 (s, 1H), 5.61 (t, J=4.6 Hz, 1H), 4.42 (s, 2H), 4.35 (d, J=4.6 Hz, 2H), 3.83-3.75 (m, 2H), 3.47-3.39 (m, 2H), 2.48 (s, 3H), 2.28 (s, 6H): MS (ES+) m/z 442.2 (M+1).

Sources & evidence

ORD record
ord-b6eb0eaa147b4516bc6ec6f96ee15f26
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…