HCID 86662231, compound → 2-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanamine hydrochloride

HRID 1627301Notes

Reaction equation

HRID 1627301 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:38]=[C:37]([F:39])[C:10]([CH2:11][S:12][C:13]2[N:14]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:15]([C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([O:28][CH3:29])[CH:22]=3)([CH3:20])[CH3:19])=[CH:16][N:17]=2)=[C:9]([F:40])[CH:8]=1)=[N+]=[N-]>CCO.Cl.O=[Pt]=O>[ClH:27].[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]([C:15]2[N:14]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:13]([S:12][CH2:11][C:10]3[C:9]([F:40])=[CH:8][C:7]([O:6][CH2:5][CH2:4][NH2:1])=[CH:38][C:37]=3[F:39])=[N:17][CH:16]=2)([CH3:20])[CH3:19])=[CH:22][C:23]=1[O:28][CH3:29]

Participants

5

Reactant 1

HCID 86662231HCID 86662231, compound

Product 1

HCID 667399852-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanamine hydrochlorideYield 173%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A pressure bottle was charged with a solution of 2-(4-(2-azidoethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (340 mg, 0.56 mmol) in EtOH (10 mL), conc HCl (0.5 mL) and PtO2 (170 mg). The bottle was purged with hydrogen (2×40 psi), pressurized with hydrogen (45 psi) and was agitated for 5 h. The reaction mixture was filtered through Celite™ and the filtrate was evaporated to give a residue. The residue was triturated with ether, and the solids were collected by filtration and dried to give the title compound (290 mg, 99%). 1H NMR (400 MHz, CD3OD) δ 7.21 (s, 1H), 7.17 (d, J=8.24 Hz, 1H), 6.76 (t, 2H), 6.55 (m, 1H), 6.51 (m, 3H), 6.29 (m, 2H), 4.07 (t, 2H), 3.83 (s, 2H), 3.68 (s, 3H), 3.62 (t, 2H), 1.49 (s, 6H).

Workup

  1. customThe bottle was purged with hydrogen (2×40 psi)
  2. filtrationThe reaction mixture was filtered through Celite™
  3. customthe filtrate was evaporated
  4. customto give a residue
  5. customThe residue was triturated with ether
  6. filtrationthe solids were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-184ab9c6b53a4635b92eade396c577b6
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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