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 2426789노트

반응식

HRID 2426789 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-112a6a4e43a140b8a8abe35438d910c7
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968552B2

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