Benzoyl chloride → HCID 22172595, compound

HRID 1823676Notes

Reaction equation

HRID 1823676 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-ade1bae67bc34ef9bb581c10ffea9ca7
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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