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

HRID 1928484Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

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.).

Workup

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

Sources & evidence

ORD record: ord-b7e98097e55f4e109de33e7716e122e4
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183262B2

Reaction notes

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