Ethyl 5-(aminomethyl)furan-2-carboxylate hydrochloride → Ethyl 5-((5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamido)methyl)furan-2-carboxylate

HRID 560894Notes

Reaction equation

HRID 560894 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.Cl.[NH2:49][CH2:50][C:51]1[O:55][C:54]([C:56]([O:58][CH2:59][CH3:60])=[O:57])=[CH:53][CH:52]=1>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([NH:49][CH2:50][C:51]4[O:55][C:54]([C:56]([O:58][CH2:59][CH3:60])=[O:57])=[CH:53][CH:52]=4)=[O:42])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 46785820Ethyl 5-(aminomethyl)furan-2-carboxylate hydrochlorideHCID 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 59481272Ethyl 5-((5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamido)methyl)furan-2-carboxylateYield 59%

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 ethyl 5-(aminomethyl)furan-2-carboxylate hydrochloride, the title compound was obtained as a colorless solid in 59% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.11 (d, J=3.4 Hz, 1H), 7.07-6.99 (m, 2H), 6.41 (d, J=3.4 Hz, 1H), 6.10 (br s, 2H), 4.62 (d, J=5.7 Hz, 2H), 4.43 (s, 2H), 4.36 (q, J=7.1 Hz, 2H), 3.83-3.75 (m, 2H), 3.47-3.40 (m, 2H), 2.48 (5, 3H), 1.38 (t J=7.1 Hz, 3 H); MS (ES+) m/z 508.15 (M+23).

Sources & evidence

ORD record
ord-550b208e1697498080acb3cbb11cc5f8
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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