Trifluoroacetic acid → 3-[6'-Hydroxymethyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1928484노트

반응식

HRID 1928484 반응식
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH2:37][O:38]C4CCCCO4)[N:22]=3)[CH:18]=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>[OH-].[Na+]>[OH:38][CH2:37][C:23]1[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[N:20]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)[CH:24]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68692639N-tert-butyl-3-[6'-(tetrahydro-pyran-2-yloxymethyl)-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

생성물 1

HCID 247602223-[6'-Hydroxymethyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide수율 23.4%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

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온도
23 °C

실험 절차

To the above described N-tert-butyl-3-[6′-(tetrahydro-pyran-2-yloxymethyl)-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonamide (0.550 g, 0.88 mmol) was added TFA (5 mL) and the reaction mixture was stirred at 23° C. for 18 h. The mixture was poured into 3 N NaOH-solution (100 ml) and stirred at 23° C. for 15 min, then partitioned between EtOAc and water, the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as an off-white solid (0.100 g, 23%). MS (ISP) 486.0 [(M+H)+]; mp 213° C. (dec.).

후처리

  1. stirringstirred at 23° C. for 15 min
  2. custompartitioned between EtOAc and water
  3. washthe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a crude product which
  7. customwas triturated with diethyl ether

출처 및 근거

ORD 기록
ord-b7e98097e55f4e109de33e7716e122e4
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183262B2

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