Sodium ethoxide → 4-Amino-6,7-dimethoxy-2-[(+/-)-4-(2-isopropyl-6-methoxyphenoxyacetyl)-cis-octahydro-1-quinoxalinyl]quinazoline hydrochloride

HRID 967015Notes

Reaction equation

HRID 967015 reaction equation
CC[O-].[Na+].[CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[OH:16])([CH3:7])[CH3:6].Cl.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[C:21]([N:33]2[C@@H:42]3[C@@H:37]([CH2:38][CH2:39][CH2:40][CH2:41]3)[N:36]([C:43](=[O:46])[CH2:44][Cl:45])[CH2:35][CH2:34]2)[N:20]=1>C(O)C>[ClH:45].[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[C:21]([N:33]2[C@@H:42]3[C@@H:37]([CH2:38][CH2:39][CH2:40][CH2:41]3)[N:36]([C:43](=[O:46])[CH2:44][O:16][C:9]3[C:10]([O:14][CH3:15])=[CH:11][CH:12]=[CH:13][C:8]=3[CH:5]([CH3:7])[CH3:6])[CH2:35][CH2:34]2)[N:20]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 125212842-Methoxy-6-(propan-2-yl)phenolHCID 867598614-Amino-6,7-dimethoxy-2-[4-chloroacetyl-(+/-)-cis-octahydro-1-quinoxalinyl]-quinazoline hydrochloride

Product 1

HCID 867598634-Amino-6,7-dimethoxy-2-[(+/-)-4-(2-isopropyl-6-methoxyphenoxyacetyl)-cis-octahydro-1-quinoxalinyl]quinazoline hydrochlorideYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10 ml of a freshly prepared 0.095M EtONa solution was added to a stirred solution of 0.16 g of 2-isopropyl-6-methoxyphenol in 5 ml of ethanol and stirring was continued for 0.5 hours at room temperature. The resulting solution was added dropwise in 15 minutes into a stirred solution 0.2 g of the above intermediate 4B in 50 ml of ethanol under nitrogen atmosphere. The mixture was stirred for 5 hours at room temperature and was then refluxed for 20 hours. The residue obtained after solvent evaporation was converted into the hydrochloride salt and crystallized from i-propanol to give 0.64 g (21%) of the title compound; m.p. 208-209° C.

Workup

  1. stirringThe mixture was stirred for 5 hours at room temperature
  2. temperaturewas then refluxed for 20 hours
  3. customThe residue obtained
  4. customafter solvent evaporation
  5. customcrystallized from i-propanol

Sources & evidence

ORD record
ord-bc172c044fd94a30900a77aaf3880ef4
Source dataset
uspto-grants-2005_10
Patent number
US06953800B2

Reaction notes

Loading…