Sodium Bicarbonate → HCID 71616921, compound

HRID 515430Notes

Reaction equation

HRID 515430 reaction equation
[N+:1]([C:4]1[O:8][C:7](/[CH:9]=[N:10]/[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[O:27][C:26](=[O:28])[NH:25][N:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[N+:1]([C:4]1[O:8][C:7]([CH2:9][NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]4[O:27][C:26](=[O:28])[NH:25][N:24]=4)[CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178518789HCID 178518789, compound

Product 1

HCID 71616921HCID 71616921, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

5-[1-(4-[(E)-1-(5-Nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9a, 0.38 g, 1 mmol) on reduction with sodiumcyano borohydride (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-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (10a, 315 mg, 82%).

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-f07c90c046fb4c86b036cf8df8488d1d
Source dataset
uspto-grants-2015_08
Patent number
US09108960B2

Reaction notes

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