Hexanoyl chloride → HCID 86653135, compound

HRID 1258578Notes

Reaction equation

HRID 1258578 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.[C:25](Cl)(=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([CH2:23][NH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 86653133HCID 86653133, compound

Product 1

HCID 86653135HCID 86653135, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methanamine (0.21 g, 0.649 mmol, 1 eq.) in 2 ml of DCM was added TEA (0.197 g, 1.94 mmol, 3 eq.) followed by hexanoyl chloride (0.131 g, 0.974 mmol, 1.5 eq.). The reaction was stirred 4 h at room temperature and the solvent was evaporated. The crude was purified by chromatography on silica gel to give N-({6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}methyl)hexanamide (0.182 g, 62% yield) as a white solid.

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-08bbd88fea4c4efe8097cc6468b6cf03
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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