Water → HCID 19039973, compound

HRID 1684635Notes

Reaction equation

HRID 1684635 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[CH:13]=2)[O:8][CH2:7]1.[H-].[Na+].Cl[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][C:28]([Cl:34])=[CH:29][CH:30]=2)[N:25]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[CH:33][C:24]([CH2:23][O:16][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH2:7][CH:6]([CH2:5][C:4]3[CH:3]=[C:2]([NH2:1])[CH:19]=[CH:18][CH:17]=3)[CH2:15]4)=[N:25]2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109548447-Chloro-2-(chloromethyl)quinolineHCID 19039972HCID 19039972, compound

Product 1

HCID 19039973HCID 19039973, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 350 mg (1.37 mmole) of the product from Example 140 in 10 mL dimethylformamide at 0° C. was added 60 mg (1.51 mmole) sodium hydride. The mixture was stirred at 0° C. for 30 minutes, then 349 mg (1.64 mmole) 2-(chloromethyl)-7-chloroquinoline was added. The mixture was warmed to room temperature and stirred for 72 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 40% ethyl acetate in hexanes yielded 476 mg (81%) of the title product as a solid, mp 128°-130° C. Analysis calculated for C26H23N2O2Cl: C, 72.47; H, 5.38; N, 650. Found: C, 72.47; H, 5.12; N, 6.43.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 72 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil

Sources & evidence

ORD record
ord-84635348c31b4f9ebd4573e0fe4059f1
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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