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

HRID 707523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 707523
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]
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Komponenten

7

Edukt 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

Produkt 1

HCID 118162492(6-(3-(4-Ethylpiperazin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanolAusbeute 110,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7c5d9b3d7e3842a89e2b9662bf1c83b2
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174998B2

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