Chloroform → 3'-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(1-ethylpiperidin-3-yl)-2-methylbiphenyl-4-carboxamide

HRID 2426789Notes

Reaction equation

HRID 2426789 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]([OH:29])=O)=[CH:23][C:22]=3[CH3:30])[CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.[CH2:33]([N:35]1[CH2:40][CH2:39][CH2:38][CH:37]([NH2:41])[CH2:36]1)[CH3:34].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].C(Cl)(Cl)Cl>C1COCC1.CO>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[O:4][N:3]1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:41][CH:37]4[CH2:38][CH2:39][CH2:40][N:35]([CH2:33][CH3:34])[CH2:36]4)=[O:29])=[CH:23][C:22]=3[CH3:30])[CH:18]=[CH:19][CH:20]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 980943-amino-N-ethylpiperidineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 577873303'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2-methylbiphenyl-4-carboxylic acid

Product 1

HCID 577871073'-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(1-ethylpiperidin-3-yl)-2-methylbiphenyl-4-carboxamideYield 25.1%

Reagents, catalysts & solvents 1

HCID 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 1-ethylpiperidine-3-amine (5.8 mg). DMT-MM (12 mg) was added, followed by overnight stirring at room temperature. Thereafter, chloroform was added to the reaction liquid, and the organic layer was washed with water. 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 3′-({4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-N-(1-ethylpiperidin-3-yl)-2-methylbiphenyl-4-carboxamide (3.4 mg).

Workup

  1. additionmixed solution
  2. washthe organic layer was washed with water
  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-112a6a4e43a140b8a8abe35438d910c7
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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