Diisopropylethylamine → 1-(bis(4-fluorophenyl)methyl)-4-(3-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propyl)piperazine

HRID 387141Notes

Reaction equation

[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH3:14])=[CH:10][C:9]([CH2:15][CH2:16][CH:17]=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:39][C:36]1[CH:35]=[CH:34][C:33]([CH:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[N:27]2[CH2:28][CH2:29][N:30]([CH2:17][CH2:16][CH2:15][C:9]3[CH:10]=[C:11]([CH2:12][CH2:13][CH3:14])[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH2:31][CH2:32]2)=[CH:38][CH:37]=1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 1529321-(Bis(4-fluorophenyl)methyl)piperazine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399313-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propanal

Product 1

HCID 685566271-(bis(4-fluorophenyl)methyl)-4-(3-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propyl)piperazine

Procedure

128 mg (71%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-phenyl-5-propyl-1H-pyrazol-3-yl)propanal (80 mg, 0.330 mmol), 1-(bis(4-fluorophenyl)methyl)piperazine (95 mg, 0.330 mmol), DIPEA (0.090 mL, 0.495 mmol) and NaBH(OAc)3 (210 mg, 0.990 mmol).

Workup

custom128 mg (71%) of target compound was obtained

Sources & evidence

ORD record: ord-463c26d450a34ea5a92a6c7d619c0aa6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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