Diisopropylethylamine → 1-(3-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propyl)-4-(bis(4-fluorophenyl)methyl)piperazine

HRID 387097Notes

Reaction equation

HRID 387097 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].[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+]>>[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[CH2:29][CH2:28][N:27]([CH:26]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=3)[CH2:32][CH2:31]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866399253-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 685571931-(3-(1-tert-butyl-5-(thiophene-2-yl)-1H-pyrazol-3-yl)propyl)-4-(bis(4-fluorophenyl)methyl)piperazine

Procedure

92 mg (84%) 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-(bis(4-fluorophenyl)methyl)piperazine (55 mg, 0.191 mmol), DIPEA (0.050 mL, 0.287 mmol) and NaBH(OAc)3 (121 mg, 0.573 mmol).

Workup

  1. custom92 mg (84%) of target compound was obtained

Sources & evidence

ORD record
ord-0a66d7313e7343f08e753d0f555668c4
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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