Triethylamine → 2-{4-[(4'-{[4-(Methoxymethyl)piperidin-1-yl]carbonyl}-2'-methylbiphenyl-3-yl)methoxy]benzyl}-1,2,4-oxadiazolidine-3,5-dione

HRID 2426788Notes

Reaction equation

HRID 2426788 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[O:4][N:3]1[CH2:8][C:9]1[CH:32]=[CH:31][C:12]([O:13][CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][C:22]=3[CH3:30])[CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.Cl.[CH3:34][O:35][CH2:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].C(N(CC)CC)C>C1COCC1.CO.C(Cl)(Cl)Cl>[CH3:34][O:35][CH2:36][CH:37]1[CH2:42][CH2:41][N:40]([C:27]([C:24]2[CH:25]=[CH:26][C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][O:13][C:12]4[CH:31]=[CH:32][C:9]([CH2:8][N:3]5[C:2](=[O:1])[NH:6][C:5](=[O:7])[O:4]5)=[CH:10][CH:11]=4)[CH:16]=3)=[C:22]([CH3:30])[CH:23]=2)=[O:28])[CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 172185994-(Methoxymethyl)piperidine hydrochlorideHCID 577873303'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2-methylbiphenyl-4-carboxylic acid

Product 1

HCID 577879242-{4-[(4'-{[4-(Methoxymethyl)piperidin-1-yl]carbonyl}-2'-methylbiphenyl-3-yl)methoxy]benzyl}-1,2,4-oxadiazolidine-3,5-dioneYield 66.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

3′-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2-methylbiphenyl-4-carboxylic acid (10.8 mg) was dissolved in a THF-methanol [1 ml, 4:1 (v/v)] mixed solution, and the solution was added to 4-(methoxymethyl)piperidine hydrochloride (7.5 mg). DMT-MM (12 mg) and triethylamine (20 μl) were added, followed by overnight stirring at room temperature. Thereafter, chloroform was added to the reaction liquid, and the organic layer was washed with 1 M hydrochloric acid. The organic layer was concentrated, and the residue was purified by a fractional HPLC (Waters, product name: Waters SunFire™ Prep C18OBD™ (19×100 mm, 5 μm)) to obtain 2-{4-[(4′-{[4-(methoxymethyl)piperidin-1-yl]carbonyl}-2′-methylbiphenyl-3-yl)methoxy]benzyl}-1,2,4-oxadiazolidine-3,5-dione (9.0 mg).

Workup

  1. additionmixed solution
  2. washthe organic layer was washed with 1 M hydrochloric acid
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by a fractional HPLC (Waters, product name: Waters SunFire™ Prep C18OBD™ (19×100 mm, 5 μm))

Sources & evidence

ORD record
ord-a799dca8fab640fcaf4279b0a76d28b3
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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