Diisopropylethylamine → 5-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-3-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonamide

HRID 2288991Notes

Reaction equation

[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[C:7](C2CCNCC2)[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:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=1.[NH2:37][C@H:38](C(O)=O)[CH2:39][C:40]1C=C2C(C=CC=C2)=[CH:42][CH:41]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH:40]2[CH2:39][CH2:38][N:37]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=3)[CH2:42][CH2:41]2)[CH2:7][O:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To 4-(4-ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine (0.150 g), prepared as in Intermediate 4, in dioxane is added 5-(2-chloro-ethyl)-2-methoxy-benzenesulfonamide (0.170 g), prepared as in Intermediate 1, Nal (0.012 g) and DIEA (0.274 ml). After heating at 100° C. for 18 hours, the reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution. The organic phase is washed with saturated brine, dried (NaSO4) and concentrated. The residue is dissolved in 1:1 MeOH-CH2Cl2 and preadsorbed onto silica gel. Purification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%), affords the title compound as a white solid.

Workup

customthe reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution
washThe organic phase is washed with saturated brine
dry with materialdried (NaSO4)
concentrationconcentrated
dissolutionThe residue is dissolved in 1:1 MeOH-CH2Cl2
customPurification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%)

Sources & evidence

ORD record: ord-2dface9b081c491eaa426a2f50b929d1
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090825

Reaction notes

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