Sodium Bicarbonate → HCID 71617042, compound

HRID 515435Notes

Reaction equation

HRID 515435 reaction equation
[F:1][C:2]1[CH:7]=[C:6](/[N:8]=[CH:9]/[C:10]2[O:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[O:28][C:27](=[O:29])[N:26]([CH3:30])[N:25]=2)[CH2:20][CH2:19]1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[O:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:19][CH2:20][CH:21]([C:24]2[O:28][C:27](=[O:29])[N:26]([CH3:30])[N:25]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178481744HCID 178481744, compound

Product 1

HCID 71617042HCID 71617042, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(2-Fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one (9f, 0.42 g, 1 mmol) on reduction with sodium cyanoboro hydride (0.12 g, 2 mmol) in the presence of catalytic amount of CH3COOH (3 drops) in methanol at 0° C. for 12 h. After completion of the reaction as indicated by TLC, the reaction mixture is neutralized with sodium bi carbonate and extracted into chloroform. The crude product thus obtained was purified by column chromatography using ethyl acetate-hexane (8:2) as eluant to obtain product 5-[1-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-one (10f, 358 mg, 86%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted into chloroform
  3. customThe crude product thus obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8d7d7c62c594423b84891d0937099854
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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