HCID 86662233, compound → HCID 66740366, compound

HRID 1627304Notes

Reaction equation

HRID 1627304 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:39]=[C:38]([F:40])[C:11]([CH2:12][S:13][C:14]2[N:15]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:16]([C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([O:29][CH3:30])[CH:23]=3)([CH3:21])[CH3:20])=[CH:17][N:18]=2)=[C:10]([Cl:41])[CH:9]=1)=[N+]=[N-]>CCO.Cl.O=[Pt]=O>[ClH:41].[Cl:41][C:10]1[CH:9]=[C:8]([CH:39]=[C:38]([F:40])[C:11]=1[CH2:12][S:13][C:14]1[N:15]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[C:16]([C:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([O:29][CH3:30])[CH:23]=2)([CH3:21])[CH3:20])=[CH:17][N:18]=1)[O:7][CH2:6][CH2:5][CH2:4][NH2:1]

Participants

5

Reactant 1

HCID 86662233HCID 86662233, compound

Product 1

HCID 66740366HCID 66740366, compoundYield 200.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A pressure bottle was charged with a solution of 2-(4-(3-azidopropoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (340 mg, 0.56 mmol) in EtOH (10 mL), conc HCl (1 mL) and PtO2 (170 mg). The bottle was purged with hydrogen (3×40 psi), pressurized with hydrogen (45 psi) and then agitated for 5 h. The reaction mixture was filtered through Celite™ and the filtrate was evaporated. The residue was triturated with ether, and the solids collected by filtration and dried to give the title compound (344 mg, 99% yield). 1H NMR (400 MHz, CD3OD) δ 7.21 (s, 1H), 6.87 (dd, J=10.99, 8.49 Hz, 1H), 6.76 (t, J=8.49 Hz, 2H), 6.67 (s, 1H), 6.58 (dd, J=8.15, 2.15 Hz, 1H), 6.52-6.42 (m, 2H), 6.38-6.29 (m, 2H), 4.16 (t, J=4.34 Hz, 2H), 3.98 (t, J=5.89 Hz, 2H), 3.77 (d, J=5.67 Hz, 3H), 3.50 (t, J=6.51 Hz, 2H), 2.65 (s, 2H), 2.17 (s, 1H), 2.43-2.15 (m, 3H), 1.49 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-2399e7f3eaa442d297ff25707706db27
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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