1,8-Diazabicyclo(5.4.0)undec-7-ene → N-[3-Chloro-4-(trifluoromethyl)phenyl]-4-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine-1-carboxamide

HRID 2371123Notes

Reaction equation

[CH:1]1([N:4]2[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:5]2)[CH2:3][CH2:2]1.ClC(Cl)(Cl)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([Cl:32])[CH:23]=1)=[O:20].C1CCN2C(=NCCC2)CC1>C(#N)C>[NH3:4].[Cl:32][C:24]1[CH:23]=[C:22]([NH:21][C:19]([N:14]2[CH2:15][CH2:16][N:11]([CH2:10][C@@H:6]3[CH2:7][CH2:8][CH2:9][N:4]([CH:1]4[CH2:3][CH2:2]4)[CH2:5]3)[CH2:12][CH2:13]2)=[O:20])[CH:27]=[CH:26][C:25]=1[C:28]([F:31])([F:30])[F:29]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine (67 mg), 2,2,2-trichloro-N-[3-chloro-4-(trifluoromethyl)phenyl]acetamide (102 mg) and DBU (46 mg) in acetonitrile (4 mL) was heated to 150° C. in the microwave for 10 minutes. The solution was concentrated at reduced pressure and purified by reverse phase prep HPLC eluting with a mixture of 5-95% acetonitrile in water and then SCX-2 column eluting with methanol then 7M NH3 in methanol to give the title compound as a white solid (55 mg, 41%).

Workup

concentrationThe solution was concentrated at reduced pressure
custompurified by reverse phase prep HPLC
washeluting with a mixture of 5-95% acetonitrile in water
washSCX-2 column eluting with methanol

Sources & evidence

ORD record: ord-ff89d3f8afc04591a4786f42444c183b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710224B2

Reaction notes

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