Triethylamine → HCID 178487837, compound

HRID 1007303Notes

Reaction equation

HRID 1007303 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)=[O:4].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[C:19]([CH:29]=[CH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[N:18]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:1][C:2]([F:14])([F:15])[C:3]([NH:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[C:19]([CH:29]=[CH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:18]=2)[CH2:9][CH2:8]1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 73996614HCID 73996614, compoundHCID 178511553HCID 178511553, compound

Product 1

HCID 178487837HCID 178487837, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A solution of 140 mg of cis-4-trifluoroacetylaminomethylcyclohexylamine in 15 mL of toluene was combined with 180 mg of 4-chloro-6-methoxy-2-[2-(2-pyridyl)ethenyl]quinazoline, 500 mg of triethylamine and 20 mg of 4-dimethylaminopyridine, and heated under reflux for 15 hours. After the reaction solution was distilled off, the residue was combined with water, and extracted with chloroform. After drying over magnesium sulfate and concentrating, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain 140 mg of the desirable compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. distillationAfter the reaction solution was distilled off
  4. extractionextracted with chloroform
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationconcentrating
  7. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-293f1149d5ac4378973ad39fc3cc178b
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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