Sodium Bicarbonate → HCID 70874808, compound

HRID 2172270Notes

Reaction equation

HRID 2172270 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[N+:13]([C:16]1[N:17]=[C:18]2[N:23]([CH:24]=1)[CH2:22][CH2:21][C@H:20]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]3)=[CH:29][CH:28]=1)[O:19]2)([O-:15])=[O:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCCl>[N+:13]([C:16]1[N:17]=[C:18]2[N:23]([CH:24]=1)[CH2:22][CH2:21][C@H:20]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][CH:36]([NH:8][C:7]4[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=4)[CH2:35][CH2:34]3)=[CH:29][CH:28]=1)[O:19]2)([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 70874615HCID 70874615, compound

Product 1

HCID 70874808HCID 70874808, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

4-(Trifluoromethoxy)aniline (1.271 ml) was added to a 1,2-dichloroethane solution (50 ml) of 1-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-one (2.5 g). Subsequently, sodium triacetoxyborohydride (1.992 g) and acetic acid (0.538 ml) were added thereto and the mixture was stirred at room temperature for 21 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) and recrystallized from ethyl acetate to afford the title compound as a yellow powder (2.55 g).

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-19a9bb5aaf0a48089107a58fa2c7006c
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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