Pyridine → HCID 18932756, compound

HRID 1597968Notes

Reaction equation

HRID 1597968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=2)[CH2:17][CH2:16]1.N1C=CC=CC=1.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:31](=[O:33])[CH3:32])[CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54313644HCID 54313644, compound

Product 1

HCID 18932756HCID 18932756, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-6-ylamine (99 mg, 0.307 mmol; from Example 30) and pyridine (32 μL, 0.620 mmol) in CHCl3 (5 mL) was added acetyl chloride (33 μL, 0.455 mmol). The mixture was refluxed 2 hours, diluted with CHCl3 (15 mL), and the organic solution was washed with saturated aqueous NaHCO3, dried over Na2SO4(s), filtered and concentrated in vacuo. Flash chromatography on silica (5% MeOH/CHCl3) afforded 77 mg of product. (M.P. 223°-229° C. (dec); GC-MS: 364 (M+); anal. RP18-HPLC RT: 3.42 min.).

Workup

  1. temperatureThe mixture was refluxed 2 hours
  2. washthe organic solution was washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5d3ce88978b4340879d001bb90bbec6
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…