Methanol → 4-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(3-pyrrolidin-1-ylpropyl)piperazin-1-yl]carbonyl}-1,3,4-oxadiazol-2-yl)methyl]benzenesulfonamide

HRID 469089

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28]([N:31]([CH2:33][C:34]2[O:38][C:37]([C:39](OC)=[O:40])=[N:36][N:35]=2)[CH3:32])(=[O:30])=[O:29])=[C:23]([CH3:43])[CH:22]=1.CO>C1COCC1>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28]([N:31]([CH3:32])[CH2:33][C:34]2[O:38][C:37]([C:39]([N:12]3[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH2:14][CH2:13]3)=[O:40])=[N:36][N:35]=2)(=[O:30])=[O:29])=[C:23]([CH3:43])[CH:22]=1

Participants

Conditions

Temperature: -40 °C

Procedure

1-(3-Pyrrolidin-1-ylpropyl)piperazine (128 mg, 1.65 mmol) was dissolved in THF (5 mL) and the resulting solution was cooled to −40° C. prior to the addition of trimethylaluminium (2 M in toluene, 0.59 mL). The reaction was stirred for 15 min at −40° C. and a solution of methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (200 mg, 0.54 mmol) in THF (5 mL) was added dropwise. The reaction was stirred at ambient temperature for 18 h and MeOH (5 mL) was added. The solvents were removed in vacuo and the resulting residue was purified by FCC, eluting with 0-2% MeOH in DCM to afford the title compound as a pale yellow semi solid.

Workup

stirringThe reaction was stirred at ambient temperature for 18 h
customThe solvents were removed in vacuo
customthe resulting residue was purified by FCC
washeluting with 0-2% MeOH in DCM

Sources & evidence

ORD record: ord-2281eb1867284a5ca0e93fe9947c5ae1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623859B2

Linked notes

Loading…