(1,3-Benzoxazol-2-ylmethyl)amine hydrochloride → N-(benzo[d]oxazol-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamide

HRID 560890Notes

Reaction equation

HRID 560890 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.[O:49]1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2[N:51]=[C:50]1[CH2:58][NH2:59]>>[O:49]1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2[N:51]=[C:50]1[CH2:58][NH:59][C:41]([C:39]1[S:40][C:36]([N:33]2[CH2:34][CH2:35][N:31]([CH2:30][C:29]3[CH:28]=[CH:27][C:26]([F:25])=[CH:47][CH:46]=3)[C:32]2=[O:45])=[CH:37][C:38]=1[CH3:44])=[O:42]

Participants

4

Reactant 3

HCID 45595356(1,3-Benzoxazol-2-ylmethyl)amine 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 25096697N-(benzo[d]oxazol-2-ylmethyl)-5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxamideYield 85%

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]oxazol-2-ylmethanamine hydrochloride, the title compound was obtained as an off-white solid in 85% yield: 1H NMR (300 MHz, CDCl3) δ 7.74-7.68 (m, 1H), 7.56-7.49 (m, 1H), 7.40-7.24 (m, 4H), 7.09-6.99 (m, 2H), 6.50 (t, J=4.6 Hz, 1H), 6.14 (s, 1H), 4.88 (d, J=4.6 Hz, 2H), 4.44 (s, 2H), 3.85-3.76 (m, 2H), 3.49-3.39 (m, 2H), 2.53 (s, 3H); MS (ES+) m/z 465.2 (M+1), 487.2 (M+23).

Sources & evidence

ORD record
ord-94917d5827cf4cfbb7f4886314d52399
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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