Potassium Carbonate → HCID 10151956, compound

HRID 2068077Notes

Reaction equation

HRID 2068077 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](Cl)=[N:19][CH:20]=[N:21]3)=[CH:16][C:15]=2[O:25][CH3:26])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[OH:27][C:28]1[CH:29]=[C:30]2[C:34](=[N:35][CH:36]=1)[NH:33][CH:32]=[CH:31]2.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([O:27][C:28]4[CH:29]=[C:30]5[C:34](=[N:35][CH:36]=4)[NH:33][CH:32]=[CH:31]5)=[N:19][CH:20]=[N:21]3)=[CH:16][C:15]=2[O:25][CH3:26])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olHCID 58960221HCID 58960221, compound

Product 1

HCID 10151956HCID 10151956, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 7-[3-(4-allylpiperazin-1-yl)propoxy]-4-chloro-6-methoxyquinazoline (288 mg, 0.76 mmol), 5-hydroxy-7-azaindole (113 mg, 0.84 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (116 mg, 0.84 mmol) in DMA (8 ml) was stirred at 85° C. for 3 hours and allowed to cool to ambient temperature. The mixture was filtered, the filtrate evaporated under vacuum and the residue purified by column chromatography eluting with methylene chloride/methanol (saturated with ammonia) (100/8/1). The volatiles were removed under vacuum to give a white solid which was triturated with diethyl ether, filtered and dried to give 7-[3-(4-allylpiperazin-1-yl)propoxy]-4-(7-azaindol-5-yloxy)-6-methoxyquinazoline (280 mg, 77%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated under vacuum
  5. customthe residue purified by column chromatography
  6. washeluting with methylene chloride/methanol (saturated with ammonia) (100/8/1)
  7. customThe volatiles were removed under vacuum
  8. customto give a white solid which
  9. customwas triturated with diethyl ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-91b27a9f94874c1a83dd15758737c83b
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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