(1-methyl-1H-pyrrol-2-yl)methanamine → 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((1-methyl-1H-pyrrol-2-yl)methyl)thiophene-2-carboxamide

HRID 2067672

Reaktionsgleichung

Reaktionsgleichung von HRID 2067672
C[C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9](CCOC3C=CC=CC=3)[C:8]2=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.CN1C=CC=C1CN>>[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:9][CH2:10][C:11]4[N:7]([CH3:8])[CH:5]=[CH:6][CH:2]=4)=[O:43])=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1

Komponenten

4

Edukt 3

HCID 2776207(1-methyl-1H-pyrrol-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

Produkt 1

HCID 594812495-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methyl-N-((1-methyl-1H-pyrrol-2-yl)methyl)thiophene-2-carboxamideAusbeute 26 %

Versuchsvorschrift

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-pyrrol-2-yl)methanamine, the title compound was obtained as a colorless solid in 26% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.99 (m, 2H), 6.61 (s, 1H), 6.13-6.03 (m, 3H), 5.71 (t, J=4.6 Hz, 1H), 4.55 (d, J=4.6 Hz, 2H), 4.42 (s, 2H), 3.83-3.75 (m, 2H), 3.61 (s, 3H), 3.47-3.39 (m, 2H), 2.48 (s, 3H); MS (ES+) m/z 427.2 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-d9fd097d1f9c47ab87b19b96f3e6e134
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293768B2

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