Sodium Bicarbonate → HCID 178483072, compound

HRID 1984870Notes

Reaction equation

HRID 1984870 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.Cl.[CH2:16]([O:23][C:24](=[O:34])[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32][NH2:33])[CH2:28][CH2:27]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>CC(O)C.C(Cl)(Cl)Cl.CO>[CH2:16]([O:23][C:24](=[O:34])[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32][NH:33][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)[CH2:28][CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 178479229HCID 178479229, compound

Product 1

HCID 178483072HCID 178483072, compoundYield 38.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine (1.50 g, 7.22 mmol) and trans-(4-aminomethyl-cyclohexyl)-carbamic acid benzyl ester hydrochloride (2.59 g, 8.67 mmol) in 2-propanol (15 mL) was stirred at reflux for 8 days and dissolved in CHCl3 and MeOH. The mixture was 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 (H-silica gel, 33% EtOAc in hexane) to give trans-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexyl}-carbamic acid benzyl ester (1.20 g, 38%) as a pale yellow solid.

Workup

  1. temperatureat reflux for 8 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 (H-silica gel, 33% EtOAc in hexane)

Sources & evidence

ORD record
ord-736a80afb0234f77a1e7df4fdff2f368
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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