Pyridine → Pentyl{4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate

HRID 875193Notes

Reaction equation

HRID 875193 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](=[N:14][O:15][CH2:16][C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1.[C:29](Cl)(=[O:36])[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[CH2:31]([O:30][C:29](=[O:36])[NH:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:6]2[O:5][CH:4]=[N:3][C:2]=2[CH3:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:18]=1)[CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69489Pentyl chloroformateHCID 910959194-[({[(4-Methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino-}oxy)methyl]-1,3-thiazol-2-amine

Product 1

HCID 91258044Pentyl{4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (95 mg, 0.3 mmol) in dichloromethane (2 mL) were added pyridine (36 mg, 0.45 mmol) and after 15 min stirring pentyl carbonochloridoate (91 mg, 0.6 mmol). After stirring at room temperature for 4 h the mixture was passed through a cartridge filled with basic alumina and 1 g silica. After rinsing with dichloromethane the final compound was eluted with heptane/ethylacetate (1/1) to afford after purification on silica pentyl {4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy) methyl]-1,3-thiazol-2-yl}carbamate (60 mg, 44%).

Workup

  1. additionfilled with basic alumina and 1 g silica
  2. washAfter rinsing with dichloromethane the final compound
  3. washwas eluted with heptane/ethylacetate (1/1)
  4. customto afford
  5. customafter purification on silica pentyl {4-[({[(4-methyl-1,3-oxazol-5-yl)(phenyl)methylene]amino}oxy) methyl]-1,3-thiazol-2-yl}carbamate (60 mg, 44%)

Sources & evidence

ORD record
ord-7a19658303d841829f04ce28baf4e07d
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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