Sodium Hydroxide → 1-[2-(6-Chloro-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 445163Notes

Reaction equation

HRID 445163 reaction equation
[OH:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]#[CH:18])=[CH:12][CH:13]=2)[C:8]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[N:7][C:6]1=[O:28].[OH-].[Na+].Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][Cl:42]>ClCCl>[Cl:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][O:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]#[CH:18])=[CH:12][CH:13]=2)[C:8]([C:19]2[CH:20]=[CH:21][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:23][CH:24]=2)=[N:7][C:6]1=[O:28]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 805161-Bromo-6-chlorohexane2×HCID 102241931-(2-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Product 1

HCID 601128261-[2-(6-Chloro-hexyloxy)-benzyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 482 mg (1.13 mmol) 1-(2-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in 2 ml dichloromethane is added 1 ml 1M aqueous NaOH. After stirring for 5 minutes the solvents are evaporated. The residue is dissolved in 4.8 ml DMEU and 0.25 ml (1.70 mmol) 1-bromo-6-chlorohexane are added. After stirring for 3 days at rt additional 0.083 ml 1-bromo-6-chlorohexane are added and stirring at rt is continued for 1 day. The reaction mixture is poured onto water, extracted with ethyl acetate and purified by flash chromatography (hexanes/ethyl acetate 6:1).

Workup

  1. customare evaporated
  2. dissolutionThe residue is dissolved in 4.8 ml DMEU
  3. additionare added
  4. stirringstirring at rt
  5. waitis continued for 1 day
  6. additionThe reaction mixture is poured onto water
  7. extractionextracted with ethyl acetate
  8. custompurified by flash chromatography (hexanes/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-2a5ae667d2b44d9fb2a80288d56c9c18
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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