(2-Thienylmethyl)amine → HCID 25096191, compound

HRID 560884Notes

Reaction equation

HRID 560884 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.[S:48]1[CH:52]=[CH:51][CH:50]=[C:49]1[CH2:53][NH2:54]>>[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:54][CH2:53][C:49]4[S:48][CH:52]=[CH:51][CH:50]=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 34005(2-Thienylmethyl)amineHCID 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 25096191HCID 25096191, compoundYield 82%

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 thiophen-2-ylmethanamine, the title compound was obtained as a colorless solid in 82% yield: mp 128-131° C.; 1H NMR (300 MHz, CDCl3) δ 7.30-7.20 (m, 3H), 7.06-6.93 (m, 4H), 6.08 (s, 1H), 6.01 (t, J=5.4 Hz, 1 H), 4.73 (d, J=5.4 Hz, 2H), 4.42 (s, 2H), 3.82-3.74 (m, 2H), 3.47-3.39 (m, 2H), 2.49 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.1, 162.4 (d, JC-F=246.4 Hz), 155.8, 142.5, 141.4, 140.9, 131.8 (JC-F=3.1 Hz), 130.0 (JC-F=8.2 Hz), 126.9, 126.1, 125.2, 119.3, 115.7 (JC-F=21.5 Hz), 112.4, 47.4, 42.7, 41.4, 38.5, 16.1; MS (ES+) m/z 452.3 (M+23).

Sources & evidence

ORD record
ord-4942791d91764eaeb87ee39f2b857d31
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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