1,8-Diazabicyclo(5.4.0)undec-7-ene → (2R,5S)-4-(4-Cyano-3-methoxyphenyl)-2,5-dimethyl-N-(6-trifluoromethyl-3-pyridyl)piperazine-1-carboxamide

HRID 1445482Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:13])OC)=[CH:5][CH:4]=1.[CH3:16][C@H:17]1[CH2:22][NH:21][C@H:20]([CH3:23])[CH2:19][N:18]1[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:32][CH3:33])[CH:25]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([N:18]2[C@@H:17]([CH3:16])[CH2:22][N:21]([C:10]([NH:9][C:6]3[CH:7]=[N:8][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=3)=[O:13])[C@H:20]([CH3:23])[CH2:19]2)=[CH:25][C:26]=1[O:32][CH3:33])#[N:29]

Participants

Conditions

Temperature: 100 °C

Procedure

Into 5 ml of toluene were dissolved 500 mg of methyl 6-(trifluoromethyl)pyridin-3-ylcarbamate and 557 mg of 4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrile, and then 0.03 ml of DBU was added thereto, followed by heating to 100° C. and 8 hours of stirring. The reaction solution was concentrated and the residue was subjected to silica gel column chromatography to obtain 450 mg of the title compound from an eluate using chloroform-methanol (96:4, v/v).

Workup

concentrationThe reaction solution was concentrated

Sources & evidence

ORD record: ord-badd1e69609b43b8aafcfe4aa0d69adc
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666873B2

Reaction notes

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