Triethylamine → HCID 21948330, compound

HRID 2214829Notes

Reaction equation

HRID 2214829 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.C(N(CC)CC)C.Cl.[CH2:18]([O:20][C:21]([NH:23][C:24]1([CH2:30][N:31]2[CH2:36][CH2:35][N:34]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH:46]=[CH2:47])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH2:33][C:32]2=[O:48])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:22])[CH3:19]>C(O)C>[CH2:18]([O:20][C:21]([NH:23][C:24]1([CH2:30][N:31]2[CH2:36][CH2:35][N:34]([S:37]([C:40]3[CH:41]=[CH:42][C:43]([CH:46]=[CH2:47])=[CH:44][CH:45]=3)(=[O:38])=[O:39])[CH2:33][C:32]2=[O:48])[CH2:25][CH2:26][N:27]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=2)[CH2:28][CH2:29]1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2763167(4-Chloropyridin-2-yl)methanolHCID 21948280HCID 21948280, compound

Product 1

HCID 21948330HCID 21948330, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-(hydroxymethyl)pyridine (118 mg), triethylamine (500 mg) and ethanol (15 ml) were added to 1-{1-{[4-ethoxycarbonylamino-4-piperidinyl]methyl}-4-(4-vinylbenzenesulfonyl)-2-piperazinone hydrochloride (200 mg), to react at 150° C. for 15 hours in a sealed tube. The reaction solution was concentrated, a 10% aqueous sodium carbonate solution was added to the residue, the mixture was extracted with dichloromethane, dried, and concentrated. The resulting residue was dried, concentrated, purified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1), and crystallized from ether to obtain the title compound (40 mg) as pale yellow crystals.

Workup

  1. customto react at 150° C. for 15 hours in a sealed tube
  2. concentrationThe reaction solution was concentrated
  3. additiona 10% aqueous sodium carbonate solution was added to the residue
  4. extractionthe mixture was extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was dried
  8. concentrationconcentrated
  9. custompurified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1)
  10. customcrystallized from ether

Sources & evidence

ORD record
ord-f776a0d65ed34255ac9eaada06026fc6
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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