1-(2,3-Xylyl)piperazine → 1-(3-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propyl)-4-(2,3-dimethylphenyl)piperazine

HRID 387093Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][C:7]([CH2:15][CH2:16][CH:17]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.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[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][C:7]([CH2:15][CH2:16][CH2:17][N:30]2[CH2:31][CH2:32][N:27]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[C:20]=3[CH3:19])[CH2:28][CH2:29]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 705411-(2,3-Xylyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399253-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 250646511-(3-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propyl)-4-(2,3-dimethylphenyl)piperazine

Procedure

86 mg (96%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propanal (50 mg, 0.191 mmol), 1-(2,3-dimethylphenyl)piperazine (36 mg, 0.191 mmol), DIPEA (0.050 mL, 0.287 mmol) and NaBH(OAc)3 (121 mg, 0.573 mmol).

Workup

custom86 mg (96%) of target compound was obtained

Sources & evidence

ORD record: ord-b56d16a4b3254f939b0f3512b8826c7a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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