Water → HCID 67975437, compound

HRID 45792Notes

Reaction equation

HRID 45792 reaction equation
[CH3:1][S:2][C:3]1[N:12]=[CH:11][C:10]2[CH:9]=[CH:8][C:7]3[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:14][NH:15][C:6]=3[C:5]=2[N:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][CH2:29][N:30]([CH3:32])[CH3:31].O>CN(C)C=O>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][N:15]1[C:6]2[C:5]3[N:4]=[C:3]([S:2][CH3:1])[N:12]=[CH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 178642-BromoethyldimethylamineHCID 178470475HCID 178470475, compound

Product 1

HCID 67975437HCID 67975437, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (150 mg, 0.52 mmol) in dry dimethylformamide (4 ml) was added cesium carbonate (339 mg 1.04 mmol) followed by 2-bromo-N,N-dimethylethanamine (135 mg 0.88 mmol). The heterogeneous mixture was stirred at room temperature for 24 hours. The mixture was treated with water and extracted with EtOAc. The organic layer washed with brine, dried over Na2SO4 and concentrated. The crude was purified by silica gel chromatography eluting with EtOAc/Ethanol 85/15 to give ethyl 1-[2-(dimethylamino)ethyl]-8-(methylsulfanyl)-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate as the major isomer (60 mg 32%) 1H NMR (401 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.16 (d, J=8.67 Hz, 1H), 7.83 (d, J=8.79 Hz, 1H), 5.29 (t, J=6.59 Hz, 1H), 4.32-4.49 (m, 2H), 2.94 (br. s., 2H), 2.71 (s, 3H), 2.24 (br. s., 6H), 1.41 (t, J=7.08 Hz, 3H); and

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel chromatography
  6. washeluting with EtOAc/Ethanol 85/15

Sources & evidence

ORD record
ord-bd654bfa6c884eda856ebd08eed4b986
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Reaction notes

Loading…