Dichloromethane → HCID 86759736, compound

HRID 2182551Notes

Reaction equation

HRID 2182551 reaction equation
C1CCN([C:7](/N=N/C(N2CCCCC2)=O)=[O:8])CC1.O[C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[N:25][C:26](OC)=[N:27]2)=[CH:22][CH:21]=1.C1(OCCO)CCCC1.C(P(CCCC)CCCC)CCC.C(Cl)[Cl:55]>CCOCC>[ClH:55].[CH3:7][O:8][C:24]1[C:23]2[C:28](=[CH:29][CH:20]=[CH:21][CH:22]=2)[N:27]=[CH:26][N:25]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 131875202-(Cyclopentyloxy)ethan-1-olHCID 136399837HCID 136399837, compound

Product 1

HCID 86759736HCID 86759736, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-(Azodicarbonyl)dipiperidine (355 mg, 1.4 mmol) was added in portions to a mixture of 44-chloro-2-fluoroanilino)-7-hydroxy-methoxyquinazoline (I 50 mg, 0.47 mmol), (prepared as described for the starting material in Example 2), 2-(cyclopentyloxy)ethanol (91 mg, 0.7 mmol), (U.S. Pat. No. 4,515,814), and tributylphosphine (284 mg, 1.4 mmol) in methylene chloride (6 ml) at 0° C. The mixture was then allowed to warm to ambient temperature and stirred for 3.5 hours. Ether (3 ml) was added and the insolubles were removed by filtration and the volatiles were removed from the filtrate by evaporation. The residue was dissolved in acetone and 1M ethereal hydrogen chloride (0.6 ml) was added. The mixture was left to stand for 60 hours and the precipitate was collected by filtration, washed with acetone and dried to give 44-chloro-2-fluoroanilino)-72-cyclopentyl xyethoxy)-4-methoxyquinazoline hydrochloride (130 mg, 60%).

Workup

  1. custom(prepared
  2. customat 0° C
  3. customthe insolubles were removed by filtration
  4. customthe volatiles were removed from the filtrate by evaporation
  5. dissolutionThe residue was dissolved in acetone
  6. addition1M ethereal hydrogen chloride (0.6 ml) was added
  7. waitThe mixture was left
  8. waitto stand for 60 hours
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with acetone
  11. customdried

Sources & evidence

ORD record
ord-f468ebb7b5a242c2ae43886d535a358b
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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