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

HRID 387034Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:18][CH2:19][CH:20]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:26]=[CH:27][C:28]=1[CH3:29].CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[CH:8][C:7]([CH2:18][CH2:19][CH2:20][N:33]2[CH2:34][CH2:35][N:30]([C:25]3[CH:26]=[CH:27][C:28]([CH3:29])=[C:23]([CH3:22])[CH:24]=3)[CH2:31][CH2:32]2)=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 27237821-(3,4-Xylyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399193-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 250660871-(3-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propyl)-4-(3,4-dimethylphenyl)piperazine

Procedure

118 mg (80%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-3-yl)propanal (85 mg, 0.297 mmol), 1-(3,4-dimethylphenyl)piperazine (57 mg, 0.297 mmol), DIPEA (0.078 mL, 0.446 mmol) and NaBH(OAc)3 (189 mg, 0.891 mmol).

Workup

custom118 mg (80%) of target compound was obtained

Sources & evidence

ORD record: ord-d4cdb7f6d86a43b1a5e33a0f0d60a88e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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