Trimethylaluminum → HCID 178495784, compound

HRID 1092121Notes

Reaction equation

HRID 1092121 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][CH2:32][C:33]2[CH:34]=[C:35]([NH2:38])[NH:36][N:37]=2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1.C[Al](C)C>C1(C)C=CC=CC=1>[CH3:30][O:29][C:27]1[CH:26]=[C:25]([CH2:31][CH2:32][C:33]2[CH:34]=[C:35]([NH:38][C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([CH:8]4[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:9]4)=[CH:20][CH:19]=3)[NH:36][N:37]=2)[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 66589759Methyl 4-(1-(2-methoxyethyl)piperidin-4-yl)benzoateHCID 178489815HCID 178489815, compound

Product 1

HCID 178495784HCID 178495784, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-[1-(2-methoxyethyl)piperidin-4-yl]benzamide was prepared following the procedure as outlined for Example 99, starting from methyl 4-(1-(2-methoxyethyl)piperidin-4-yl)benzoate (0.428 g, 1.25 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.309 g, 1.25 mmol) and 2M trimethylaluminium (1.56 mL, 3.13 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 afford the title compound (0.215 g, 34.9%) as an off white solid.

Workup

  1. customN-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-[1-(2-methoxyethyl)piperidin-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-22360b7607cf401d91b2ed29ce386f7f
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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