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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 1445482
Notes
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Reaction equation

HRID 1445482 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23082060Methyl [6-(trifluoromethyl)pyridin-3-yl]carbamateHCID 686912044-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrile

Product 1

HCID 10320641(2R,5S)-4-(4-Cyano-3-methoxyphenyl)-2,5-dimethyl-N-(6-trifluoromethyl-3-pyridyl)piperazine-1-carboxamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes