3-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid → HCID 178428032, compound

HRID 560909Notes

Reaction equation

HRID 560909 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](O)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[C:48]([C:52]1[NH:56][N:55]=[C:54]([CH2:57][NH2:58])[CH:53]=1)([CH3:51])([CH3:50])[CH3:49]>>[C:48]([C:52]1[NH:56][N:55]=[C:54]([CH2:57][NH:58][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:42])[CH:53]=1)([CH3:51])([CH3:49])[CH3:50]

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 178441040HCID 178441040, compound

Product 1

HCID 178428032HCID 178428032, compoundYield 41%

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 (5-tert-butyl-1H-pyrazol-3-yl)methanamine, the title compound was obtained as a colorless solid in 41% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.99 (m, 2H), 6.42 (t, J=5.4 Hz, 1H), 6.10 (s, 1H), 6.05 (s, 1H), 4.55 (d, J=5.4 Hz, 2H), 4.42 (s, 2H), 3.83-3.75 (m, 2H), 3.47-3.39 (m, 2 H), 2.49 (s, 3H), 1.32 (s, 9H); MS (ES+) m/z 470.2 (M+1).

Sources & evidence

ORD record
ord-bfda5fbc603e496b9080e638fdd145f4
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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