HCID 13804713, compound → HCID 90417304, compound

HRID 929490Notes

Reaction equation

HRID 929490 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9]2=[O:26])=[CH:4][CH:3]=1>CO.[BH4-].[Na+]>[OH:13][CH:12]1[N:8]([C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[C:9](=[O:26])[C:10]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:11]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 13804713HCID 13804713, compound

Product 1

HCID 90417304HCID 90417304, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4311764Sodium borohydrideSolvent

Procedure

After the addition of compound 4e (1.00 g, 2.78 mmol) in methanol, NaBH4 was slowly added thereto in acetone-ice bath and the agitation for 3 hours was carried out at room temperature. After the identification of disappearance of compound 4e with TLC, quenching was carried out with in HCL aqueous solution in the ice bath. Then, three times extractions were carried out with EA and three times washings were carried out with brine. Water was removed by using Na2SO4, solvents were removed and then, the column chromatography was carried out with EA/HX (¼). After the distillation under the reduced pressure, vacuum drying was carried out to obtain compound 8

Workup

  1. additionwas slowly added
  2. customAfter the identification of disappearance of compound 4e with TLC, quenching
  3. extractionThen, three times extractions
  4. customWater was removed
  5. customwere removed
  6. distillationAfter the distillation under the reduced pressure, vacuum
  7. customdrying

Sources & evidence

ORD record
ord-945ac268ff9c405aad3bb8b37d331ee6
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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