Cesium carbonate → HCID 11370694, compound

HRID 602318Notes

Reaction equation

HRID 602318 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:22])[N:8]3[CH2:21][CH2:20][CH2:19][CH:9]3[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]=2[CH:12]=1.Br[CH2:24][CH2:25]CCCC(Cl)=O.BrCCCCC1NC(=O)C2C(=CC(OC)=CC=2)N1C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:22])[N:8]3[CH2:21][CH2:25][CH2:24][CH2:20][CH2:19][CH:9]3[N:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 898486-Bromohexanoyl chlorideHCID 11358349HCID 11358349, compoundHCID 66645914HCID 66645914, compound

Product 1

HCID 11370694HCID 11370694, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure for 6-methoxy-4-phenyl-2,3,3a,4-tetrahydropyrrolo[2,1-b]quinazolin-9(1H)-one, using 6-bromohexanoyl chloride in place of 4-bromobutyryl chloride, 410 mg of an intermediate presumed to be 2-(4-bromobutyl)-7-methoxy-1-phenyl-2,3-dihydroquinazolin-4(1H)-one. 200 mg of this material was dissolved in 2 mL DMF and treated with cesium carbonate (450 mg). The reaction was stirred at room temp for 72 h, then partitioned between EtOAc and water. The organic solution was dried (Na2SO4) and concentrated. Flash chromatography (50% EtOAc in hexanes) gave the titled compound.

Workup

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-37cf3e4e8ba3401a8848edcf550ae3cc
Source dataset
uspto-grants-2011_03
Patent number
US07906521B2

Reaction notes

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