Acetic Acid → HCID 178452070, compound

HRID 1711427Notes

Reaction equation

HRID 1711427 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:24]([N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl>[C:27]([O:26][C:24]([N:31]1[CH2:36][CH2:35][CH:34]([NH:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:13])=[O:12])[CH2:33][CH2:32]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 178507365HCID 178507365, compound

Product 1

HCID 178452070HCID 178452070, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [3-(1-naphthylsulfonyl)-1H-indazol-5-yl]amine (400 mg, 1.24 mmol), 1-Boc-4-piperidone (493 mg, 2.47 mmol), sodium triacetoxyborohydride (524 mg, 2.47 mmol), and acetic acid (149 mg, 2.47 mmol) in 1,2-dichloroethane was stirred at room temperature overnight, diluted with CH2Cl2, washed with water, dried over Na2SO4 and concentrated in vacuo. The resultant residue was purified by column chromatography with 1% MeOH in CH2Cl2 as eluent to provide the title compound, 390 mg (62% yield), characterized by HNMR and mass spectral analyses.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by column chromatography with 1% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-c01d498e74a341d1a0cc0c41d30f169c
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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