HCID 11282733, compound → HCID 59768224, compound

HRID 2217323Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][C:8]2[O:9][CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=2)=[CH:5][CH:4]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:28]2([CH2:33][NH:34]C(C3N=C(CC4C=CC(OC)=CC=4)SC=3)=O)[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]>>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:28]2([CH2:33][NH:34][C:13]([C:11]3[N:12]=[C:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=4)[O:9][CH:10]=3)=[O:15])[CH2:29][CH2:30][CH2:31][CH2:32]2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

Reactant 2

HCID 11282733HCID 11282733, compound

HCID 667238322-(4-Methoxybenzyl)oxazole-4-carboxylic Acid

Product 1

HCID 59768224HCID 59768224, compoundYield 66%

Procedure

Starting from 2-(4-Methoxy-benzyl)-oxazole-4-carboxylic acid 25 g, 0.1 mmol) and [2-(3,4-Dimethoxy-phenyl)-2-methyl]-propylamine (47 mg, 0.2 mmol) following a similar procedure reported for the preparation of 2-(4-Methoxy-benzyl)-thiazole-4-carboxylic acid[1-(3,4-dimethoxy-phenyl)-cyclopentylmethyl]-amide, the amide (30 mg, 66%) was obtained as a white solid. ESI-MS m/Z calc. 450.5, found 451.2(M+1)+. Retention time of 3.51 minutes 1H NMR (400 MHz, CDCl3) δ1.68-2.19 (m, 8H), 3.50 (d, J=6.3 Hz, 2H), 3.81 (s, 3H), 3.88 (s, 3H), 3.92 (s, 3H), 4.00 (s, 2H), 6.73-6.88 (m, 6H), 7.20 (d, J=8.7 Hz, 2H), 8.07 (s, 1H).

Sources & evidence

ORD record: ord-4a41539e0e1e446f8273e87c460e1101
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407976B2

Reaction notes

Loading…