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Diphenylmethane → (6-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanol

HRID 707523
Notes
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Reaction equation

HRID 707523 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:14][CH:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH3:22])[CH2:17][CH2:16]2)[CH2:12]1.C(C1C=CC=CC=1)C1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O.CN1C(=O)CCC1>[CH2:21]([N:18]1[CH2:19][CH2:20][N:15]([CH:13]2[CH2:12][N:11]([C:2]3[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=3[F:10])[CH2:14]2)[CH2:16][CH2:17]1)[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7580DiphenylmethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 627863071-(Azetidin-3-yl)-4-ethylpiperazineHCID 112692767(6-Chloro-5-fluoropyridin-2-yl)methanol

Product 1

HCID 118162492(6-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanolYield 110.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixed solution of a commercially available product of (6-chloro-5-fluoropyridin-2-yl)methanol (200 mg, 1.24 mmol) and NMP (2.00 mL) were added a mixture (627 mg) of 1-(azetidin-3-yl)-4-ethylpiperazine and benzylbenzene described in Production Example 1-3-2 and DBU (565 mg, 3.71 mmol) at room temperature. The resultant mixture was irradiated with a microwave at 180° C. for 8 hours. The reaction mixture was cooled to room temperature, then water was added thereto, and the resultant solution was extracted with dichloromethane. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 and subsequently ethyl acetate) to give a crude product (402 mg) of the title compound.

Workup

  1. extractionthe resultant solution was extracted with dichloromethane
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-7c5d9b3d7e3842a89e2b9662bf1c83b2
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174998B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes