Triethylamine → HCID 21948300, compound

HRID 2214830Notes

Reaction equation

HRID 2214830 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl.[CH2:17]([O:19][C:20]([NH:22][C:23]1([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH:45]=[CH2:46])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH2:32][C:31]2=[O:47])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:21])[CH3:18]>C(O)C>[NH2:1][C:2]1[CH:7]=[C:6]([N:26]2[CH2:27][CH2:28][C:23]([CH2:29][N:30]3[CH2:35][CH2:34][N:33]([S:36]([C:39]4[CH:40]=[CH:41][C:42]([CH:45]=[CH2:46])=[CH:43][CH:44]=4)(=[O:38])=[O:37])[CH2:32][C:31]3=[O:47])([NH:22][C:20]([O:19][CH2:17][CH3:18])=[O:21])[CH2:24][CH2:25]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5818662-Amino-4-chloropyridineHCID 21948280HCID 21948280, compound

Product 1

HCID 21948300HCID 21948300, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-chloropyridine (132 mg), triethylamine (700 mg) and ethanol (15 ml) were added to 1-{[4-ethoxycarbonylamino-4-piperidinyl]methyl}-4-(4-vinylbenzensulfonyl)-2-piperazinone hydrochloride (250 mg), to react at 155° C. for 20 hours in a sealed tube. The reaction solution was concentrated, a 10% aqueous sodium carbonate solution was added to the residue, the material 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 dichloromethane-hexane to obtain the title compound (58 mg) as pale yellow crystals.

Workup

  1. customto react at 155° C. for 20 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 material 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 dichloromethane-hexane

Sources & evidence

ORD record
ord-2f7ecb92e34348f98281fd809f5a3ab3
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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