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

Potassium Iodide → N-Cyclopropyl-4-oxazol-5-yl-N-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-benzamide

HRID 1424540
Notes
Print preview

Reaction equation

HRID 1424540 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25](O)([CH3:27])[CH3:26])[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[F:29][C:30]([F:41])([F:40])C1(COS(C)(=O)=O)CC1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN1CCCC1=O.O.C(OCC)(=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3([C:30]([F:41])([F:40])[F:29])[CH2:27][CH2:26]3)[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 86649942(1-(Trifluoromethyl)cyclopropyl)methyl methanesulfonateHCID 86709612N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Product 1

HCID 73053286N-Cyclopropyl-4-oxazol-5-yl-N-[1-(1-trifluoromethyl-cyclopropylmethyl)-piperidin-4-yl]-benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide (80 mg), methanesulfonic acid (1-trifluoromethyl-cyclopropyl)methyl ester (269 mg), K2CO3 (81 mg), and potassium iodide (38 mg) in N-methyl-2-pyrrolidone (3 mL) is stirred at 100° C. for two days. After cooling to room temperature, ethyl acetate and water are added to the mixture. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel [dichloromethane/7 M ammonia in methanol 9:1→7:3] and the crude product is purified by preparative HPLC to give the title compound. LC (method 3): tR=1.22 min; Mass spectrum (ESI+): m/z=434 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel [dichloromethane/7 M ammonia in methanol 9:1→7:3]
  6. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-f0eb1f100e33481dbc991eb271efab0d
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927726B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes