Sodium Carbonate → HCID 20556255, compound

HRID 1105674Notes

Reaction equation

HRID 1105674 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:28](=[O:29])[CH2:27][C:26]3([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:25][C:24]2=[O:35])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:16].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([CH:22]2[CH2:21][CH:20]([N:23]3[C:28](=[O:29])[CH2:27][C:26]4([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]4)[CH2:25][C:24]3=[O:35])[CH2:19][CH2:18][NH:17]2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 12822555HCID 12822555, compound

Product 1

HCID 20556255HCID 20556255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 2.39 g of 4-amino-2-chloro-6,7-dimethoxyquinazoline, 2.64 g of 3-(4-piperidinyl)-3-azaspiro-[5,5]-undecan-2,4-dione, 2.1 g anhydrous sodium carbonate and 25 ml of dimethylformamide is stirred under nitrogen at 150° for 10 hours. It is filtered, the filtrate evaporated, the residue dissolved in methylene chloride, the solution washed with aqueous sodium carbonate, dried, filtered and evaporated. The residue is triturated with 50 ml of isopropanol, the remainder taken up in isopropanol and the mixture acidified with hydrogen chloride, to yield the 3-[2-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]-3-azaspiro[5,5]undecan-2,4-dione monohydrochloride melting at 290° (dec.).

Workup

  1. filtrationIt is filtered
  2. customthe filtrate evaporated
  3. dissolutionthe residue dissolved in methylene chloride
  4. washthe solution washed with aqueous sodium carbonate
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is triturated with 50 ml of isopropanol

Sources & evidence

ORD record
ord-2bf033223324495f870a1a995b04baf4
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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