Methanol → HCID 18932757, compound

HRID 1597992Notes

Reaction equation

HRID 1597992 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][NH:25]2)=[CH:21][CH:20]=1.N1C=CC=CC=1.CO>ClCCCl.Cl.CCOCC>[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][CH2:24][N:25]2[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 2585676-Chloro-2,3-dihydro-1h-indoleHCID 21717193153437-50-4

Product 1

HCID 18932757HCID 18932757, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Chloro-6-morpholino-quinazoline (382 mg, 1.53 mmol) and 6-chloroindoline (258 mg, 1.63 mmol) were heated at reflux in 8 mL of 1,2-dichloroethane and pyridine (264 mg, 3.36 mmol) for 16 hours. The reaction mixture was vacuum evaporated and partitioned between 100 mL of ethyl acetate and 50 mL of 5% sodium bicarbonate. The organic layer was washed with an additional 50 mL of bicarbonate and 50 mL of brine, dried with magnesium sulfate, filtered and evaporated in vacuo to a residue. This was purified by flash chromatography on silica gel eluted with 20% acetone/methylene chloride. The pure solid isolated from the column was converted to its hydrochloride salt by dissolution in methanol containing 1.1 equivalents of anhydrous hydrogen chloride and precipitation with ether; 396 mg (65%); M.P. 277°-279° C.

Workup

  1. customevaporated
  2. custompartitioned between 100 mL of ethyl acetate and 50 mL of 5% sodium bicarbonate
  3. washThe organic layer was washed with an additional 50 mL of bicarbonate and 50 mL of brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue
  7. customThis was purified by flash chromatography on silica gel
  8. washeluted with 20% acetone/methylene chloride
  9. customThe pure solid isolated from the column

Sources & evidence

ORD record
ord-ccf452fc80514026b71c86f51555e72e
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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