Hexanal → HCID 86653144, compound

HRID 1258592Notes

Reaction equation

HRID 1258592 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9](=[N:16][O:17][CH2:18][C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)[C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C([O-])(O)=O.[Na+]>[CH2:26]([NH:25][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:18][O:17][N:16]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=2)[C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[N:24]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 6184HexanalHCID 5049666Sodium triacetoxyborohydrideHCID 86653142HCID 86653142, compound

Product 1

HCID 86653144HCID 86653144, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 6-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine (134 mg, 0.38 mmol) in dry dichloromethane (5 mL) were added capronaldehyde (52.9 mg, 0.53 mmol) and sodium triacetoxyborohydride (151 mg, 0.68 mmol) at room temperature. After stirring at room temperature for 20 h, the reaction mixture was diluted with dichloromethane (10 mL) and aq. NaHCO3 (10 g/L, 10 mL) was added. After phase separation, the organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded N-hexyl-6-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine as a colourless oil [115 mg, yield 69%; HPLC/MS: m/z=440 (M+H); logP(HCOOH)=2.78].

Workup

  1. additionwas added
  2. customAfter phase separation
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-ff4ada6ac4d44a5d8a09ee1fecee06a6
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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