(4-methylthiophen-2-yl)methanamine → HCID 25097188, compound

HRID 2067678Notes

Reaction equation

HRID 2067678 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.[CH3:48][C:49]1[CH:50]=[C:51]([CH2:54][NH2:55])[S:52][CH:53]=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:51]4[S:52][CH:53]=[C:49]([CH3:48])[CH:50]=4)=[O:43])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 2795528(4-methylthiophen-2-yl)methanamineHCID 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 25097188HCID 25097188, compoundYield 80%

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 (4-methylthiophen-2-yl)methanamine, the title compound was obtained as a colorless solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.24 (m, 2H), 7.08-6.98 (m, 2H), 6.82 (s, 1H), 6.78 (s, 1H), 6.09 (s, 1H), 5.96 (t, J=5.2 Hz, 1H), 4.66 (d, J=5.2 Hz, 2H), 4.42 (s, 2H), 3.83-3.75 (m, 2H), 3.47-3.39 (m, 2H), 2.49 (s, 3H), 2.22 (s, 3H); MS (ES+) m/z 444.1 (M+1).

Sources & evidence

ORD record
ord-1b34f80283594086b1148d05145bc6d5
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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