Trimethylaluminum → HCID 178456213, compound

HRID 16847Notes

Reaction equation

HRID 16847 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][C:32]2[CH:33]=[C:34]([NH2:37])[NH:35][N:36]=2)[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.C[Al](C)C>C1(C)C=CC=CC=1>[CH3:29][O:28][C:26]1[CH:25]=[C:24]([CH2:30][CH2:31][C:32]2[CH:33]=[C:34]([NH:37][C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]([CH:7]4[CH2:6][CH2:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH2:9][CH2:8]4)=[CH:19][CH:18]=3)[NH:35][N:36]=2)[CH:23]=[C:22]([O:21][CH3:20])[CH:27]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 66589778HCID 66589778, compoundHCID 178489815HCID 178489815, compound

Product 1

HCID 178456213HCID 178456213, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(1-prop-2-enylpiperidin-4-yl)benzamide was prepared following the procedure as outlined for Example 99, starting from methyl 4-(1-prop-2-enylpiperidin-4-yl)benzoate (0.259 g, 1.00 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.247 g, 1 mmol) and 2M trimethylaluminium (1.250 mL, 2.50 mmol) in toluene (10 ml). The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 5% 2.5M ammonia/methanol in DCM. Pure fractions were evaporated to dryness and the product was crystallised from DCM/diethyl ether to give on filtration the title compound (0.182 g, 38.3%) as a white solid.

Workup

  1. customN-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(1-prop-2-enylpiperidin-4-yl)benzamide was prepared
  2. customThe crude product was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 5% 2.5M ammonia/methanol in DCM
  4. customPure fractions were evaporated to dryness
  5. customthe product was crystallised from DCM/diethyl ether

Sources & evidence

ORD record
ord-2f1a67f9558541d8bd5974bda6ccfb29
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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