3-Pyridinecarboxaldehyde → HCID 57664584, compound

HRID 1467873Notes

Reaction equation

HRID 1467873 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:30][C:26]3[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=3)[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57664584HCID 57664584, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (150 mg, 0.43 mmol) and pyridine-3-carboxaldehyde (46 mg, 0.43 mmol) in dichloroethane was added sodium triacetoxyborohydride (128 mg, 0.60 mmol, 1.4 eq.). The reaction mixture was stirred at room temperature for 12 hours. After this period, the solution was decanted and purified by flash chromatography to give the title compound 19 as a yellow oil. 1H NMR (CDCl3): δ 8.55-8.48 (m, 2H), 8.15-8.11 (m, 1H), 8.08-8.02 (m, 1H), 7.87-7.81 (m, 1H), 7.71-7.59 (m, 1H), 7.25-7.20 (m, 1H), 3.92-3.81 (m, 1H), 3.48 (s, 2H), 2.91-2.81 (m, 2H), 2.10-1.87 (m, 5H), 1.56-1.45 (m, 2H), 1.01-0.94 (m, m, 2H), 0.82-0.74 (m, 2H). LC: 100%. MS (EI): m/z 440 (M+H+).

Workup

  1. waitAfter this period
  2. customthe solution was decanted
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-bf4ebbfc991641099ddab97d7333e2aa
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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