Sodium Bicarbonate → HCID 86635351, compound

HRID 657087Notes

Reaction equation

HRID 657087 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[N:10][C:9](=[O:12])[N:8]([CH2:13][CH:14]=O)[C:7]=2[CH:16]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[N:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:17]3[CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]3)[C:7]=2[CH:16]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635352HCID 86635352, compound

Product 1

HCID 86635351HCID 86635351, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of [6-(methyloxy)-3-oxo-1,2,4-benzotriazin-4(3H)-yl]acetaldehyde (as the methyl hemiacetal) (89 mg, 0.346 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (69 mg, 0.346 mmol) in chloroform (5 ml) and MeOH (0.5 ml) was stirred for 2 h before addition of NaBH(OAc)3 (220 mg, 1.038 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (20 ml). The reaction was then extracted with 20% MeOH in DCM (3×100 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-5% MeOH/DCM gradient to provide the desired compound (48 mg, 34%).

Workup

  1. extractionThe reaction was then extracted with 20% MeOH in DCM (3×100 ml)
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customthe crude residue purified by chromatography on silica gel using a 0-5% MeOH/DCM gradient

Sources & evidence

ORD record
ord-763130526c724c43b9fd359d540dd323
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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