Diisopropylethylamine → 2-(5-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonylamino)-acetamide

HRID 2288993Notes

Reaction equation

[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[C:7]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].Cl[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:39][CH3:40])=[C:29]([S:31]([NH:34][CH2:35][C:36]([NH2:38])=[O:37])(=[O:33])=[O:32])[CH:30]=1.[Li+].[Br-].C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[C:7]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:39][CH3:40])=[C:29]([S:31]([NH:34][CH2:35][C:36]([NH2:38])=[O:37])(=[O:33])=[O:32])[CH:30]=3)[CH2:18][CH2:17]2)[O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine (450 mg, 1.4 mmol), prepared as in Intermediate 4, and 2-[5-(2-chloro-ethyl)-2-methoxy-benzenesulfonylamino]-acetamide (644 mg), prepared as in Intermediate 6, LiBr (182 mg), and diisopropyl ethylamine (0.73 mL) in dioxane (15 mL) is stirred at 100° C. for 18 h. The solvent is evaporated and the residue purified by chromatography on silica using 3% MeOH:CHCl3 as eluent to afford the product as a white foam.

Workup

customThe solvent is evaporated
customthe residue purified by chromatography on silica using 3% MeOH

Sources & evidence

ORD record: ord-5bb2b484cbf84aa38ecfc1e74a9963ff
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090825

Reaction notes

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