Sodium Bicarbonate → HCID 68581553, compound

HRID 2237599Notes

Reaction equation

HRID 2237599 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:3]=1.[C:18]([O:22][C:23]([NH:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@@H:27]1[NH2:32])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C.CN(C)C1C=CN=CC=1>[CH2:16]([O:15][C:13]([C:4]1[N:3]=[C:2]([NH:32][C@H:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C@H:26]2[NH:25][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=1)=[O:14])[CH3:17]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamineHCID 23068383Ethyl 4-chloro-6-methylquinazoline-2-carboxylate

Product 1

HCID 68581553HCID 68581553, compoundYield 108.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 8.47 g of 4-chloro-2-ethoxycarbonyl-6-methylquinazoline and 7.60 g of (1S,2R)-2-(t-butoxycarbonylamino)cyclohexylamine in 350 ml of toluene, 11.8 ml of triethylamine and a catalytic amount of 4-dimethylaminopyridine were added, and then the mixture was heated at reflux for 16 hours. After the reaction solution was mixed with a saturated sodium hydrogencarbonate solution and extracted with chloroform, the organic layer was washed with a 10% citric acid solution and saturated brine. After drying over magnesium sulfate, the solvent was distilled off to obtain 15.7 g of the desirable compound as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. extractionextracted with chloroform
  4. washthe organic layer was washed with a 10% citric acid solution and saturated brine
  5. dry with materialAfter drying over magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-44772eab154f48a683666e4640e43760
Source dataset
uspto-grants-2010_05
Patent number
US07718663B2

Reaction notes

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