Sodium Bicarbonate → HCID 178483065, compound

HRID 1984867Notes

Reaction equation

HRID 1984867 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:15]([O:19][C:20](=[O:31])[NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][NH2:30])[CH2:25][CH2:24]1)([CH3:18])([CH3:17])[CH3:16].C([O-])(O)=O.[Na+]>CC(O)C>[C:15]([O:19][C:20](=[O:31])[NH:21][CH2:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][NH:30][C:2]2[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:27][CH2:28]1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 178453600HCID 178453600, compound

Product 1

HCID 178483065HCID 178483065, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine (15.2 g, 73.3 mmol) and trans-(4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (14.8 g, 61.0 mmol) in 2-propanol (80 mL) was stirred at reflux for 4 days, poured into saturated aqueous NaHCO3, and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 33% EtOAc in hexane) to give trans-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-butyl ester (20.4 g, 81%) as a pale yellow solid.

Workup

  1. temperatureat reflux for 4 days
  2. extractionthe aqueous layer was extracted with CHCl3 (three times)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (NH-silica gel, 33% EtOAc in hexane)

Sources & evidence

ORD record
ord-c1636413e3aa42d382a6cbcc176dcb1f
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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