Sodium Bicarbonate → HCID 67171478, compound

HRID 1630385Notes

Reaction equation

HRID 1630385 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[N:7][C:8]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:9][CH:10]=2)[N:5]1[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39](O)([CH3:41])[CH3:40])[N:34]=1)[CH:2]=[CH2:3].COCCN(S(F)(F)[F:53])CCOC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[N:7][C:8]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:9][CH:10]=2)[N:5]1[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:53])([CH3:41])[CH3:40])[N:34]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67169472HCID 67169472, compound

Product 1

HCID 67171478HCID 67171478, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

16 mg of the compound obtained in Example 92 was dissolved in 3 mL of chloroform, and 0.1 mL of bis(2-methoxyethyl)aminosulfur trifluoride was added thereto and stirred at room temperature for 1 hour. Aqueous saturated sodium hydrogencarbonate solution was added to it and extracted with chloroform. The chloroform layer was washed with saturated saline water, dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. This was purified through column chromatography (ethyl acetate/chloroform=3/1) and then solidified from ethyl acetate/hexane solution to obtain 8 mg of the entitled compound as a yellow solid.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with saturated saline water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThis was purified through column chromatography (ethyl acetate/chloroform=3/1)

Sources & evidence

ORD record
ord-187d6c6c20e247ffb468c28b06f72fc4
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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