Dimethylformamide → 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thio phen-2-sulfonic acid methyl-[2-(4-methylpiperazin-1-yl)ethyl]amide

HRID 1792621Notes

Reaction equation

HRID 1792621 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH3:54])[S:5]([C:8]1[S:9][C:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]4[C:24]([C:47]5[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=5)=[N:25][N:26]([C:28]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:27]=4)[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[CH:11][CH:12]=1)(=[O:7])=[O:6].[CH3:55][N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1.C(N(CC)CC)C.CN(C)C=O>O.C(OCC)(=O)C>[CH3:54][N:4]([CH2:3][CH2:2][N:59]1[CH2:60][CH2:61][N:56]([CH3:55])[CH2:57][CH2:58]1)[S:5]([C:8]1[S:9][C:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]4[C:24]([C:47]5[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=5)=[N:25][N:26]([C:28]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:27]=4)[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[CH:11][CH:12]=1)(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 23537718HCID 23537718, compound

Product 1

HCID 688137505-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thio phen-2-sulfonic acid methyl-[2-(4-methylpiperazin-1-yl)ethyl]amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 100 mg 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thiophen-2-sulfonic acid (2-chloroethyl)methylamide (compound in Example 746), 29 μL 1-methyl piperazine, 72 μl triethylamine and 3 mL N,N-dimethylformamide was stirred at 110° C. for 24 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and brine and dried over sodium sulfate, and the solvent was evaporated. The residue was purified by NH silica gel column chromatography (hexane/ethylacetate)to give 41 mg 5-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]quinazolin-4-yl}thio phen-2-sulfonic acid methyl-[2-(4-methylpiperazin-1-yl)ethyl]amide. This product was reacted in the same manner as in Example 68, to give 28 mg of the title compound as yellow crystals.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by NH silica gel column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-0ae23b425b964445bada4355cbe1525e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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