Water → HCID 178486878, compound

HRID 2384542Notes

Reaction equation

HRID 2384542 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[O:7]=[C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[C:15]([OH:18])[CH:16]=2)[N:11]=[CH:10][NH:9]1.CS(O[C@H:26]1[CH2:31][CH2:30][C@H:29]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[C:34](=[O:39])[CH2:33]2)[CH2:28][CH2:27]1)(=O)=O.O>CN1CCCC1=O>[O:7]=[C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[C:15]([O:18][C@H:26]3[CH2:27][CH2:28][C@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[C:34](=[O:39])[CH2:33]4)[CH2:30][CH2:31]3)[CH:16]=2)[N:11]=[CH:10][NH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1354464136-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-oneHCID 178481023HCID 178481023, compound

Product 1

HCID 178486878HCID 178486878, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2.4 g sodium carbonate are added to 2 g of 3,4-dihydro-4-oxo-6-hydroxy-7-methoxy-quinazoline (VII) in 16 ml N-methyl-2-pyrrolidinone at 130° C. Then six times 600 mg (in total: 2.4 g) (trans)-1-methanesulphonyloxy-4-(4-methyl-3-oxo-piperazin-1-yl)-cyclohexane (II) are added stepwise at 130° C. within 4 h and the mixture is kept at 130° C. for 20 h. After 10 days, 25 ml of water are added and the mixture is extracted with 25 ml isopropyl acetate, 50 ml of dichloromethane and 25 ml of dichloromethane. The organic phases are evaporated down and the residue is separated off by preparative HPLC. 500 mg of the product are obtained.

Workup

  1. waitAfter 10 days
  2. extractionthe mixture is extracted with 25 ml isopropyl acetate, 50 ml of dichloromethane and 25 ml of dichloromethane
  3. customThe organic phases are evaporated down
  4. customthe residue is separated off by preparative HPLC

Sources & evidence

ORD record
ord-fa352776a7e644e2b2d4e3b2ade124d5
Source dataset
uspto-grants-2012_09
Patent number
US08263768B2

Reaction notes

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