Potassium Iodide → HCID 59682931, compound

HRID 1668692Notes

Reaction equation

HRID 1668692 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([O:24][C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[NH:30][C:29]([CH3:34])=[CH:28]5)=[N:19][CH:20]=[N:21]3)=[CH:16][C:15]=2[O:35][CH3:36])[CH2:7][CH2:6]1)=[O:4].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.[I-].[K+]>CN(C=O)C>[CH3:36][O:35][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:14]=1[O:13][CH2:12][CH2:11][N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:10][CH2:9]1)[N:21]=[CH:20][N:19]=[C:18]2[O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH3:34])=[CH:28]2

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 59682922HCID 59682922, compound

Product 1

HCID 59682931HCID 59682931, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-{2-[4-(chloroacetyl)piperazin-1-yl]ethoxy}-6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline (0.130 g), pyrrolidine (0.04 ml), potassium iodide (0.01 g) and DMF (3.5 ml) was stirred and heated to 80° C. for 1 hour. The mixture was cooled to ambient temperature, the solvent evaporated under vacuum and the residue was purified by column chromatography on silica using increasingly polar solvent mixtures, starting with dichloromethane and ending with dichloromethane/methanol saturated with ammonia (3.5M) (95/5). Evaporation of the solvents gave a foam, which was triturated under ether to give 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-{2-[4-(pyrrolidin-1-ylacetyl)piperazin-1-yl]ethoxy}quinazoline (0.09 g) as a pale yellow solid which was collected by filtration and dried under vacuum.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent evaporated under vacuum
  3. customthe residue was purified by column chromatography on silica using
  4. temperatureincreasingly polar solvent mixtures
  5. customEvaporation of the solvents
  6. customgave a foam, which
  7. customwas triturated under ether

Sources & evidence

ORD record
ord-81119e13efbf4ec1bb3301fe9f4384eb
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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