Triethylamine → HCID 23298083, compound

HRID 1953419Notes

Reaction equation

HRID 1953419 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:2]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH2:29][C:30]1[CH:31]=[C:32]([C:36]2[CH:37]=[C:38]([N:42]3[C:47](=[O:48])[C:46]([CH2:49][C:50]4[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=4)=[N:45][C:44]4[CH:56]=[CH:57][CH:58]=[N:59][C:43]3=4)[CH:39]=[CH:40][CH:41]=2)[CH:33]=[CH:34][CH:35]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10]([C:12]([NH:29][C:30]3[CH:31]=[C:32]([C:36]4[CH:37]=[C:38]([N:42]5[C:47](=[O:48])[C:46]([CH2:49][C:50]6[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=6)=[N:45][C:44]6[CH:56]=[CH:57][CH:58]=[N:59][C:43]5=6)[CH:39]=[CH:40][CH:41]=4)[CH:33]=[CH:34][CH:35]=3)=[O:14])[N:11]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 22724025HCID 22724025, compound

Product 1

HCID 23298083HCID 23298083, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 2-(3-pyridyl)thiazole-4-carboxylic acid (0.56 g) and triethylamine (0.55 g) in methylene chloride (25 ml) was added pivaloyl chloride (0.33 g) in methylene chloride (5 ml) and the mixture was stirred for 2 hours. After the reaction mixture was cleared, 4-[3-(3-aminophenyl)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (1.0 g) was added thereto and the mixture was stirred under reflux for 2 hours. The reaction mixture was washed with sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated. Crude residue was chromatographed on silica gel (70 g, chloroform-methanol 100:1 as eluent) to give 4-[3-[3-[2-(3-pyridyl)thiazol-4-ylcarbonylamino]phenyl]phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine as colorless crystals (0.48 g).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 2 hours
  3. washThe reaction mixture was washed with sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customCrude residue was chromatographed on silica gel (70 g, chloroform-methanol 100:1 as eluent)

Sources & evidence

ORD record
ord-acaaf5667339445b9a0506867e69a7bd
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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