Picolinic acid → HCID 86751347, compound

HRID 1292607Notes

Reaction equation

HRID 1292607 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[CH:10]1[CH:11]=[CH:12][C:13]2N(O)N=N[C:14]=2[CH:15]=1.C1CCC(N=[C:27]=[N:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31]C2)CC1.[NH2:35][CH2:36][CH2:37][S:38][CH2:39][C:40]([NH2:42])=[O:41]>ClCCl>[N:28]1([CH2:27][C:10]2[CH:15]=[C:14]([CH:13]=[CH:12][CH:11]=2)[O:9][CH2:7][CH2:2][CH2:3][CH:39]([S:38][CH2:37][CH2:36][NH:35][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[C:40]([NH2:42])=[O:41])[CH2:29][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 20430442HCID 20430442, compound

Product 1

HCID 86751347HCID 86751347, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was suspended 1.38 g (0.011 mol) of picolinic acid in 50 mg of dichloromethane and added 1.68 g (0.0 11 mol) of HOBt and 2.26 g (0.011 mol) of DCC under cooling with ice and the mixture was stirred for 30 minutes. Thereto was added 4.0 g (0.011 mol) of N-3-[3-(piperidinomethyl)phenoxy]propyl]-2-(2-aminoethylthio)acetamide and the mixture was stirred for 18 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with 10% 5 aqueous solution of sodium hydroxide and with water and dried over Glauber's salt. Then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 1.38 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. filtrationThe precipitate was filtrated off
  4. washthe filtrate was washed with 10% 5 aqueous solution of sodium hydroxide and with water
  5. dry with materialdried over Glauber's salt
  6. customThen the solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-6e4dd5f3f37f4368a99fc7a4620fbbe8
Source dataset
uspto-grants-1998_05
Patent number
US05756822

Reaction notes

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