Benzoyl chloride → HCID 22172595, compound

HRID 2055648Notes

Reaction equation

HRID 2055648 reaction equation
[CH3:1][O:2][CH:3]([O:32][CH3:33])[CH2:4][NH:5][CH:6]([C:10]1[N:11]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:12](=[O:20])[C:13]2[CH:19]=[CH:18][N:17]=[CH:16][C:14]=2[N:15]=1)[CH:7]([CH3:9])[CH3:8].[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:32][CH3:33])[CH2:4][N:5]([CH:6]([C:10]1[N:11]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:12](=[O:20])[C:13]2[CH:19]=[CH:18][N:17]=[CH:16][C:14]=2[N:15]=1)[CH:7]([CH3:9])[CH3:8])[C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22172597HCID 22172597, compound

Product 1

HCID 22172595HCID 22172595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[1-(2,2-dimethoxy-ethylamino)-2-methyl-propyl]-3-naphthalen-1-ylmethyl-3H-pyrido-[3,4-d]pyrimidin-4-one (522 mg, 1.17 mmol), benzoyl chloride (247 mg, 1.76 mmol), and triethylamine (179 mg, 1.76 mmol) in methylene chloride (10 mL) is stirred at room temperature for 18 h. The reaction is washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water, and brine. The organic layer is dried (Na2SO4) and concentrated to yield the title compound, N-(2,2-dimethoxy-ethyl)-N-[2-methyl-1-(3-naphthalen-1-ylmethyl-4-oxo-3,4-dihydro-pyrido[3,4-d]pyrimidin-2-yl)-propyl]-benzamide.

Workup

  1. washThe reaction is washed sequentially with 0.5 N HCl, water, 5% NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b459000047274da3bfbc5e03dfe51f4e
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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