Pyridine → HCID 23144205, compound

HRID 337420Notes

Reaction equation

HRID 337420 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].S(Cl)(Cl)=O.N1C=CC=CC=1.[NH2:25][C:26]1[S:27][C:28]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1>ClCCl>[CH3:14][N:2]([CH3:1])[C:3]([N:5]1[CH2:6][CH2:7][CH:8]([C:11]([NH:25][C:26]2[S:27][C:28]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[C:29]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)[N:30]=2)=[O:13])[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 50764741-(dimethylcarbamoyl)piperidine-4-carboxylic acidHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole

Product 1

HCID 23144205HCID 23144205, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(N,N-dimethylcarbamoyl)piperidine-4-carboxylic acid (300 mg, 1.50 mmol) obtained in Step 2 was dissolved in dichloromethane (15 mL), and thionyl chloride (0.547 mL, 7.50 mmol) was added thereto, followed by stirring under heating and reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in chloroform (5 mL). The resulting solution was added to a pyridine (10 mL) solution of 2-amino-4-(2-furyl)-5-morpholinothiazole (126 mg, 0.50 mmol) obtained in Step 1 of Example 29, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1) to afford the entitled Compound 55 (171 mg, 81%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in chloroform (5 mL)
  5. stirringby stirring at room temperature for 1 hour
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-0d329a6341c44218958e04b9a8dfb8e8
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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