(5-Phenyl-1,3,4-oxadiazol-2-yl)methanamine oxalate → 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)thiophene-2-carboxamide

HRID 560893Notes

Reaction equation

HRID 560893 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(O)(=O)C(O)=O.[C:54]1([C:60]2[O:64][C:63]([CH2:65][NH2:66])=[N:62][N:61]=2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[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]([NH:66][CH2:65][C:63]4[O:64][C:60]([C:54]5[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=5)=[N:61][N:62]=4)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 45925648(5-Phenyl-1,3,4-oxadiazol-2-yl)methanamine oxalateHCID 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 acid

Product 1

HCID 594812055-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)thiophene-2-carboxamideYield 67%

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-phenyl-1,3,4-oxadiazol-2-yl)methanamine oxalate, the title compound was obtained as a colorless solid in 67% yield: 1H NMR (300 MHz, CDCl3) δ 8.06-8.01 (m, 2H), 7.55-7.45 (m, 3H), 7.30-7.24 (m, 2H), 7.07-6.98 (m, 2H), 6.45 (t, J=5.4 Hz, 1H), 6.11 (s, 1H), 4.90 (d, J=5.4 Hz, 2H), 4.43 (s, 2H), 3.84-3.76 (m, 2H), 3.48-3.40 (m, 2H), 2.50 (s, 3H); MS (ES+) m/z 514.1 (M+23).

Sources & evidence

ORD record
ord-9ca7b06b4c0e4b888afcd0669c1df4de
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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