Diisopropylethylamine → 1-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-(3,4-dimethylphenyl)piperazine

HRID 387044Notes

Reaction equation

HRID 387044 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH:22]=O)[CH:10]=2)=[CH:5][CH:4]=1.[CH3:24][C:25]1[CH:26]=[C:27]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:28]=[CH:29][C:30]=1[CH3:31].CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:12]=[C:11]([CH2:20][CH2:21][CH2:22][N:35]3[CH2:36][CH2:37][N:32]([C:27]4[CH:28]=[CH:29][C:30]([CH3:31])=[C:25]([CH3:24])[CH:26]=4)[CH2:33][CH2:34]3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 27237821-(3,4-Xylyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399203-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 250663091-(3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propyl)-4-(3,4-dimethylphenyl)piperazine

Procedure

105 mg (82%) of target compound was obtained by using a method same as in Example 1 by using 3-(5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)propanal (75 mg, 0.245 mmol), 1-(3,4-dimethylphenyl)piperazine (47 mg, 0.245 mmol), DIPEA (0.064 mL, 0.368 mmol) and NaBH(OAc)3 (156 mg, 0.735 mmol).

Workup

  1. custom105 mg (82%) of target compound was obtained

Sources & evidence

ORD record
ord-07f81b5bb74c4c21964aa9887f66505c
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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