Sodium Bicarbonate → HCID 86670409, compound

HRID 1972619Notes

Reaction equation

HRID 1972619 reaction equation
[N+:1]([C:4]1[S:8][C:7]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=3)[C@@H:14]([CH2:34][N:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[S:36]([CH3:39])(=[O:38])=[O:37])[CH2:13]2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.C([O-])(O)=O.[Na+]>[Fe].C(O)(=O)C>[NH2:1][C:4]1[S:8][C:7]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([C:24]([OH:33])([C:25]([F:28])([F:26])[F:27])[C:29]([F:32])([F:31])[F:30])=[CH:20][N:19]=3)[C@@H:14]([CH2:34][N:35]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[S:36]([CH3:39])(=[O:38])=[O:37])[CH2:13]2)(=[O:10])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86670408HCID 86670408, compound

Product 1

HCID 86670409HCID 86670409, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A 20-mL vial was charged with N-(((2R)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.131 g, 0.186 mmol, step 1), iron filings (0.052 g, 0.93 mmol) and acetic acid (2 mL). The reaction mixture was heated at 50° C. for 40 min and then allowed to cool to room temperature. Saturated aqueous NaHCO3 (20 mL) was then added slowly. The aqueous phase was extracted with EtOAc (2×20 mL) and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (25 g of silica gel, 20 to 80% EtOAc in hexanes) to afford N-(((2R)-4-((5-amino-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.0912 g) as a light-yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  3. washthe combined organic phases were washed with saturated aqueous NaCl (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (25 g of silica gel, 20 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5d78d45da28d4b64aeae73fd6bd9eb05
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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