Triethylamine → HCID 69021907, compound

HRID 1007294Notes

Reaction equation

HRID 1007294 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:3]=1.[C:23]([O:27][C:28]([NH:30][C@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[NH2:37])=[O:29])([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:23]([O:27][C:28]([NH:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]1[NH:37][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:3]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 73996589HCID 73996589, compound

Product 1

HCID 69021907HCID 69021907, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A solution of 391 mg of 4-chloro-2-(4-chlorostyryl)-6-methoxyquinazoline, 379 mg of cis-2-(tert-butoxycarbonyl)aminocyclohexylamine, and 358 mg of triethylamine in 20 mL of toluene was combined with a catalytic amount of 4-dimethylaminopyridine, and heated under reflux for 20 hours. After distilling the reaction solution off, the residue was combined with water, extracted with chloroform, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (chloroform:methanol=50:1) to obtain 580 mg of the desirable compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. distillationAfter distilling the reaction solution off, the residue
  4. extractionextracted with chloroform
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-6c11069dc735424eb105bc131bdff0a9
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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