Water → HCID 22031841, compound

HRID 1792517Notes

Reaction equation

HRID 1792517 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:55][S:56](Cl)(=[O:58])=[O:57].O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:28]=[CH:27][C:25]([NH:26][S:56]([CH3:55])(=[O:58])=[O:57])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:29]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22031454HCID 22031454, compound

Product 1

HCID 22031841HCID 22031841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While 7 mL solution of 68 mg 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}aniline obtained in Example 19 and 34 mg triethylamine in dichloromethane was stirred in a stream of nitrogen, 20 μL methylsulfonyl chloride was added thereto. Then, the mixture was stirred at room temperature for 3 hours. 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 anhydrous sodium sulfate. The drying agent was filtered off, and the concentrated residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 52 mg of the title compound as a pale yellow amorphous.

Workup

  1. additionwas added
  2. extractionwas then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe concentrated residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-864de2facee847e2a759f4c38964c169
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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