Dimethylformamide → HCID 23537274, compound

HRID 1792612Notes

Reaction equation

HRID 1792612 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][N:29]=[C:28]3[N:35]2[CH2:40][CH2:39][N:38]([C:41]3[CH:42]=[C:43]([NH2:47])[CH:44]=[CH:45][CH:46]=3)[CH2:37][CH2:36]2)[CH:22]=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48](Cl)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50].C(N(CC)CC)C.CN(C)C=O>O>[CH3:50][C:49]([CH3:52])([CH3:51])[C:48]([NH:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:41]([N:38]2[CH2:39][CH2:40][N:35]([C:28]3[C:27]4[C:32](=[CH:33][CH:34]=[C:25]([C:23]5[CH:22]=[N:21][N:20]([C:1]([C:14]6[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=6)([C:2]6[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=6)[C:8]6[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=6)[CH:24]=5)[CH:26]=4)[N:31]=[CH:30][N:29]=3)[CH2:36][CH2:37]2)[CH:42]=1)=[O:53]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 23537409HCID 23537409, compound

Product 1

HCID 23537274HCID 23537274, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 mg 3-{4-[6-(1-trityl-1H-pyrazol-4-yl)quinazolin-4-yl]piperazin-1-yl} phenylamine obtained in Example 825, 30 mg pivaloyl chloride, 50 μl triethylamine and 10 mL N,N-dimethyl formamide was stirred at room temperature for 15 minutes. Water was added to the mixture which was then extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 91 mg of the title compound as a colorless oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-843565819210434bb7f5bca1637e6bb5
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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