Water → HCID 23537541, compound

HRID 1792608Notes

Reaction equation

HRID 1792608 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[S:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[C:22]([C:45]5[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=5)=[N:23][N:24]([C:26]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:25]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:5])=[O:4].[CH3:52][O:53][C:54]1[CH:55]=[C:56]([CH:61]=[CH:62][CH:63]=1)[C:57](=[O:60])[CH2:58]Br.O>O1CCCC1>[CH3:52][O:53][C:54]1[CH:55]=[C:56]([C:57](=[O:60])[CH2:58][N:2]([CH3:1])[S:3]([C:6]2[S:7][C:8]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:21]5[C:22]([C:45]6[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=6)=[N:23][N:24]([C:26]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=6)([C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:25]=5)[CH:19]=4)[N:14]=[CH:13][N:12]=3)=[CH:9][CH:10]=2)(=[O:5])=[O:4])[CH:61]=[CH:62][CH:63]=1

Participants

5

Reactant 3

HCID 962WaterHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 23537543HCID 23537543, compound

Product 1

HCID 23537541HCID 23537541, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 mg 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thiophen-2-sulfonic acid methylamide (compound in Example 745) was dissolved in 5 mL tetrahydrofuran, then 0.07 mL of 1.0 M lithium bistrimethyl silyl amide was added thereto under ice-cooling, and the mixture was stirred for 0.5 hour. Under ice-cooling, a solution of 80 mg 3-methoxyphenacyl bromide in 2 mL tetrahydrofuran was added thereto and stirred for 1.5 hour. Water was added to the reaction solution which was then extracted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 17 mg of the title compound.

Workup

  1. temperatureunder ice-cooling
  2. temperatureUnder ice-cooling
  3. stirringstirred for 1.5 hour
  4. extractionwas then extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e49151c37b1d4c0cb9b4e644de63399e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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