HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 1593393
Notes
Print preview

Reaction equation

HRID 1593393 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-a8e5c6e648354bd48430ca0b182a183a
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07297698B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes