Triethylamine → HCID 54674797, compound

HRID 2251811Notes

Reaction equation

HRID 2251811 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[CH:14][C:13]([NH:16][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=3)(=[O:28])=[O:27])=[CH:12][N:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 69145927HCID 69145927, compound

Product 1

HCID 54674797HCID 54674797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

216 mg (0.98 mmol) of 2-(4-Allylpiperazin-1-yl)pyrimidin-5-ylamine from Example 16.2 and 215 mg (0.98 mmol) of 4-isopropylbenzenesulfonyl chloride were dissolved in 20 ml of tetrahydrofuran at room temperature, after which 0.4 ml (3.0 mmol) of triethylamine was added dropwise and the mixture was stirred at room temperature overnight. After the solvent had been evaporated down to dryness, water was added to the resulting residue. The aqueous reaction mixture was made acid using 1N aqueous hydrochloric acid and extracted twice with diethyl ether. The aqueous phase was made alkaline to pH 9-10, using a 1N solution of sodium hydroxide and then extracted three times with diethyl ether. The combined organic phases were dried over sodium sulfate. The residue which was obtained after filtering off the drying agent and evaporating the solvent down to dryness was thoroughly stirred with a mixture composed of heptane and diethyl ether, filtered off with suction and dried, with 71 mg (18% of theory) of the title compound being obtained.

Workup

  1. customAfter the solvent had been evaporated down to dryness, water
  2. additionwas added to the resulting residue
  3. extractionextracted twice with diethyl ether
  4. extractionextracted three times with diethyl ether
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customThe residue which was obtained
  7. filtrationafter filtering off the drying agent
  8. customevaporating the solvent down to dryness
  9. stirringwas thoroughly stirred with a mixture
  10. filtrationfiltered off with suction
  11. dry with materialdried, with 71 mg (18% of theory) of the title compound
  12. custombeing obtained

Sources & evidence

ORD record
ord-7ba3f1fb6f704d20803109c9092768a0
Source dataset
uspto-grants-2008_01
Patent number
US07320979B2

Reaction notes

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