Triethylamine → N-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-4-nitro-benzamide

HRID 219729Notes

Reaction equation

HRID 219729 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([O-:35])=[O:34]>O1CCCC1>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:40](=[O:41])[C:39]3[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:44][CH:43]=3)[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 690260674-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamine

Product 1

HCID 69026237N-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-4-nitro-benzamideYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

0.91 g of 4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamine (2.64 mmol) and 0.53 g of triethylamine (5.28 mmol) were dissolved in 20 ml of tetrahydrofuran. 0.49 g of 4-nitro-benzoyl-chloride (2.64 mmol) were added at 0-5° C. After stirring for 2 h at 0-5° C., the solvent was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was re-extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using ethyl acetate and ethyl acetate-methanol (2%). Fractions containing the product were combined. The solvent was evaporated to yield 0.51 g of the title compound as a solid.

Workup

  1. customthe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was re-extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by chromatography on silica gel
  8. additionFractions containing the product
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e781ab6c390c420eb05c0e3b0d419482
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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