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

HRID 707523
ノート
印刷プレビュー

反応式

HRID 707523 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c5d9b3d7e3842a89e2b9662bf1c83b2
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174998B2

反応ノート

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