1-Methyl-5-aminomethylimidazole → HCID 59481227, compound

HRID 560902Notes

Reaction equation

HRID 560902 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.[CH3:48][N:49]1[C:53]([CH2:54][NH2:55])=[CH:52][N:51]=[CH:50]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:55][CH2:54][C:53]4[N:49]([CH3:48])[CH:50]=[N:51][CH:52]=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 27954241-Methyl-5-aminomethylimidazoleHCID 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 59481227HCID 59481227, compoundYield 75%

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 (1-methyl-1H-imidazol-5-yl)methanamine, the title compound was obtained as a colorless solid in 75% yield: 1H NMR (300 MHz, CDCl3) δ 7.48 (s, 1H), 7.30-7.22 (m, 2H), 7.08-6.98 (m, 3H), 6.08 (s, 1H), 5.86 (t, J=5.0 Hz, 1H), 4.59 (d, J=5.0 Hz, 2H), 4.42 (s, 2H), 3.84-3.75 (m, 2H), 3.65 (s, 3H), 3.49-3.40 (m, 2H), 2.48 (s, 3H); MS (ES+) m/z 428.2 (M+1).

Sources & evidence

ORD record
ord-4440ac8fb9114c16bfb64e5afaec372e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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