Sodium Chloride → HCID 51353249, compound

HRID 77406Notes

Reaction equation

HRID 77406 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]1[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[N:14]([CH3:27])[C:13]3=[O:28])[CH2:3][CH2:2]2.ClC1C=CC=C(C(OO)=[O:37])C=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>ClCCl>[Cl:26][C:22]1[CH:21]=[C:20]([C:15]2[N:14]([CH3:27])[C:13](=[O:28])[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([N:4]4[CH:5]5[CH2:6][CH2:7][N+:1]([O-:37])([CH2:9][CH2:8]5)[CH2:2][CH2:3]4)[CH:11]=3)[N:16]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 513526046-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-2-(3-chlorophenyl)-3-methylquinazolin-4(3H)-one

Product 1

HCID 51353249HCID 51353249, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-2-(3-chlorophenyl)-3-methylquinazolin-4(3H)-one (400 mg, 1.013 mmol) (Example 2AL) in dichloromethane (12 mL) was added 3-chloroperbenzoic acid (250 mg, 1.013 mmol) and the reaction stirred at ambient temperature for 3 h. Sodium carbonate solution was added to neutralise the acid and the aqueous saturated with sodium chloride. The organic layer was separated off and chromatographed on 10 g silica, eluting with dichloromethane with 10% ammonia in methanol (1 M). To remove the remaining impurities the mixture was purified by acidic prep hplc, product passed through a carbonate on silica cartridge (2 g) to remove the acid to afford 4-(2-(3-chlorophenyl)-3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-1,4-diazabicyclo[3.2.2]nonane 1-oxide (112 mg, 0.273 mmol).

Workup

  1. customThe organic layer was separated off
  2. customchromatographed on 10 g silica
  3. washeluting with dichloromethane with 10% ammonia in methanol (1 M)
  4. customTo remove the remaining impurities the mixture
  5. customwas purified by acidic prep hplc, product
  6. customto remove the acid

Sources & evidence

ORD record
ord-405c633d617b45fc8a11cec8e6713c4f
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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