Sodium Bicarbonate → HCID 86662223, compound

HRID 1627263Notes

Reaction equation

HRID 1627263 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[CH:39]=[CH:38][C:28]([C:29]([NH:31][CH2:32][CH2:33][S:34]([O-:37])(=[O:36])=[O:35])=[O:30])=[CH:27][C:26]=3[F:40])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:41][CH3:42].C([NH+](CC)CC)C.C([O-])(O)=O.[Na+:54]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:14]([S:23][CH2:24][C:25]3[CH:39]=[CH:38][C:28]([C:29]([NH:31][CH2:32][CH2:33][S:34]([O-:37])(=[O:35])=[O:36])=[O:30])=[CH:27][C:26]=3[F:40])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:41][CH3:42].[Na+:54]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86662221HCID 86662221, compound

Product 1

HCID 86662223HCID 86662223, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of triethylammonium 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3-fluorobenz amido)ethane sulfonate (45 mg, 0.061 mmol) in water (3 mL) was added NaHCO3 (5.1 mg, 0.061 mmol). After stirring 4 h, the aqueous mixture was washed with Et2O (5 mL). The aqueous layer was concentrated in vacuo, and the residue was triturated with DCM-MeOH (2:1=v/v, 6 mL). The mixture was filtered through Celite™ and the filtrate was concentrated in vacuo to give the title compound (25 mg, 63%) as white solid. 1H NMR (400 MHz, CD3OD): δ 7.53-7.48 (m, 2H), 7.27 (s, 1H), 7.15 (d, 1H), 7.06 (t, 1H) 6.79 (t, 2H), 6.48-6.45 (m, 2H), 6.07-6.03 (m, 2H), 4.05 (s, 2H), 3.84 (t, 2H), 3.66 (s, 3H), 3.12 (t, 2H), 1.50 (s, 6H).

Workup

  1. washthe aqueous mixture was washed with Et2O (5 mL)
  2. concentrationThe aqueous layer was concentrated in vacuo
  3. customthe residue was triturated with DCM-MeOH (2:1=v/v, 6 mL)
  4. filtrationThe mixture was filtered through Celite™
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e15029b7d3504e1bb8085ea35d466123
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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