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Ethanol → [8-(3,4-Difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

HRID 451474
ノート
印刷プレビュー

反応式

HRID 451474 の反応式
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[N:4][N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]3[N:28]=[C:29]([NH2:31])[N:30]=[C:23]23)[CH:18]=[CH:19][C:20]=1[F:21].C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C.O>[F:14][C:15]1[CH:16]=[C:17]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]3[N:28]=[C:29]([NH:31][CH:10]4[CH2:11][CH2:12][N:7]([C:5]5[O:6][C:2]([CH3:1])=[N:3][N:4]=5)[CH2:8][CH2:9]4)[N:30]=[C:23]23)[CH:18]=[CH:19][C:20]=1[F:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 4311764Sodium borohydride2 回HCID 583978531-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-oneHCID 673426828-(3,4-Difluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

生成物 1

HCID 58397875[8-(3,4-Difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 1-(5-methyl-1,3,4-oxadiazol-2-yl)piperidin-4-one (79.6 mg, 440 μmol) and 8-(3,4-difluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (110 mg, 440 mmol) in toluene (5 mL) and acetic acid (280 μL) was heated to reflux at a Dean-Stark trap. The reaction mixture was cooled to room temperature and ethanol (3 mL) was added followed by sodium borohydride (66.5 mg, 61.9 μL, 1.76 mmol). The reaction mixture was stirred at 50° C. for 3 hours. Further sodium borohydride (66.5 mg, 61.9 μL, 1.76 mmol) was added and stirred at 50° C. for 3 hours. Water was added to the reaction mixture and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, 100 g, 0% to 15% MeOH in dichloromethane, 40 minutes). The title compound was obtained as a white solid (32.8 mg, 18%). MS ISP (m/e): 416.3 (69) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.16-7.07 (m, 1H), 7.00-6.93 (m, 1H), 6.91-6.87 (m, 1H), 4.12-4.01 (m, 4H), 3.93-3.87 (m, 2H), 3.72-3.60 (m, 1H), 3.23-3.13 (m, 2H), 2.38 (s, 3H), 2.32-2.23 (m, 1H), 2.18-1.88 (m, 5H), 1.58-1.48 (m, 2H).

後処理

  1. temperatureto reflux at a Dean-Stark trap
  2. stirringstirred at 50° C. for 3 hours
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, 100 g, 0% to 15% MeOH in dichloromethane, 40 minutes)

出典と根拠

ORDレコード
ord-7e82613b6a2a4070813f87331fc4c022
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486967B2

反応ノート

読み込み中…

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