Triethylamine → HCID 69023628, compound

HRID 1007297Notes

Reaction equation

HRID 1007297 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]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=1.[C:19]([O:23][C:24]([NH:26][C@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[NH2:33])=[O:25])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:19]([O:23][C:24]([NH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]1[NH:33][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]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 22668047Ethyl 4-chloro-6-methoxyquinazoline-2-carboxylate

Product 1

HCID 69023628HCID 69023628, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.96 g of 4-chloro-2-ethoxycarbonyl-6-methoxyquinazoline in 70 mL of toluene was combined with 1.58 g of cis-2-tert-butoxycarbonylaminocyclohexylamine and 0.74 g of triethylamine, and heated under reflux for 15 hours. After concentrating, the mixture was combined with water, extracted with chloroform, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform) to obtain 2.70 g of the desirable compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. concentrationAfter concentrating
  4. extractionextracted with chloroform
  5. customdried
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-37b4df8e77f64723928f29fa98dbbe9e
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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