Piperidine → HCID 178456587, compound

HRID 892111Notes

Reaction equation

HRID 892111 reaction equation
C([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1[C:31](O)=[O:32])C1C=CC=CC=1.S(Cl)(Cl)=O.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(Cl)(Cl)Cl>[CH2:20]([C@@H:18]1[CH2:19][N:14]2[C:15]([C:16]3[NH:8][C:9]([C:31]([N:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:32])=[N:10][C:11]=3[N:12]([CH2:28][CH2:29][CH3:30])[C:13]2=[O:27])=[N:17]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 69662067HCID 69662067, compound

Product 1

HCID 178456587HCID 178456587, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Compound 47a (70 mg, 0.158 mmol) obtained in Example 47 was dissolved in chloroform (2 mL), to the solution was added thionyl chloride (40 μL, 0.548 mmol, 3.4 equivalents), and the mixture was stirred at 60° C. for 30 minutes. To the reaction solution was added piperidine (320 μL, 3.24 mmol, 20 equivalents) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated and directly purified by silica gel column chromatography (chloroform:methanol=98:2). Thereafter, the title compound (17 mg, 26%) was obtained in a manner similar to the method by which Compound 40 was obtained from Adduct 40a in Example 40.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography (chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-4d2bea95749b4bda9d907ea7cf063c76
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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