Chloroacetyl chloride → 4-Amino-6,7-dimethoxy-2-[4-chloroacetyl-(+/-)-cis-octahydro-1-quinoxalinyl]-quinazoline hydrochloride

HRID 967014Notes

Reaction equation

HRID 967014 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.Cl.[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[C:11]([N:23]2[C@@H:32]3[C@@H:27]([CH2:28][CH2:29][CH2:30][CH2:31]3)[NH:26][CH2:25][CH2:24]2)[N:10]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[ClH:1].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[C:11]([N:23]2[C@@H:32]3[C@@H:27]([CH2:28][CH2:29][CH2:30][CH2:31]3)[N:26]([C:3](=[O:4])[CH2:2][Cl:1])[CH2:25][CH2:24]2)[N:10]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 865863104-Amino-6,7-dimethoxy-2-[(+/-)-cis-octahydro-1-quinoxalinyl]-quinazoline dihydrochloride

Product 1

HCID 867598614-Amino-6,7-dimethoxy-2-[4-chloroacetyl-(+/-)-cis-octahydro-1-quinoxalinyl]-quinazoline hydrochlorideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.26 g of chloroacetyl chloride in 6 ml of methylene chloride was added dropwise over 15 minutes at 0° C. to a stirred mixture of 0.5 g of the above intermediate 4A and 0.21 g of diisopropylethylamine in 15 ml of methylene chloride. After 4-hour stirring at room temperature and 72-hour resting in a refrigerator, the solid was collected by suction and purified by crystallisation from chloroform to give 0.12 g (33%) of the desired product; m.p. >270° C.

Workup

  1. customthe solid was collected by suction
  2. custompurified by crystallisation from chloroform

Sources & evidence

ORD record
ord-34ebd8a99dc84b6aaa6df2928219c328
Source dataset
uspto-grants-2005_10
Patent number
US06953800B2

Reaction notes

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