Benzo-1,3-dioxole-5-methylamine → HCID 25096696, compound

HRID 2067669Notes

Reaction equation

HRID 2067669 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.[O:48]1[C:52]2[CH:53]=[CH:54][C:55]([CH2:57][NH2:58])=[CH:56][C:51]=2[O:50][CH2:49]1>>[O:48]1[C:52]2[CH:53]=[CH:54][C:55]([CH2:57][NH:58][C:41]([C:39]3[S:40][C:36]([N:33]4[CH2:34][CH2:35][N:31]([CH2:30][C:29]5[CH:28]=[CH:27][C:26]([F:25])=[CH:47][CH:46]=5)[C:32]4=[O:45])=[CH:37][C:38]=3[CH3:44])=[O:43])=[CH:56][C:51]=2[O:50][CH2:49]1

Participants

4

Reactant 3

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 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 25096696HCID 25096696, 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 benzo[d][1,3]dioxol-5-ylmethanamine, the title compound was obtained as a colorless solid in 82% yield: 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2H), 7.07-6.98 (m, 2H), 6.85-6.73 (m, 3H), 6.09 (s, 1H), 5.95 (s, 2H), 5.92 (t, J=5.5 Hz, 1H), 4.46 (d, J=5.5 Hz, 2H), 4.42 (s, 2H), 3.84-3.76 (m, 2H), 3.48-3.40 (m, 2H), 2.49 (s, 3H); MS (ES+) m/z 468.2 (M+1).

Sources & evidence

ORD record
ord-fe0cc51bf39648e498f52fec13ec6b8b
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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