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Diethyl Ether → 2-(3-(allyloxy)phenyl]-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-8-amine

HRID 456700
ノート
印刷プレビュー

反応式

HRID 456700 の反応式
[CH:1]1([NH:6][C:7]2[C:8]3[N:9]([C:13]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:24]=4)=[C:14]([C:16]4[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=4)[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:41](Br)[CH:42]=[CH2:43].CCOCC>CN(C)C=O.O>[CH2:43]([O:22][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:8]3[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:11]=[CH:10][N:9]3[C:13]=2[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:24]=2)[CH:21]=[CH:20][CH:19]=1)[CH:42]=[CH2:41]
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 3283Diethyl EtherHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 101390603-[8-(Cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]phenol

生成物 1

HCID 101414512-(3-(allyloxy)phenyl]-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-8-amine収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}phenol (12 mg, 0.03 mmol) in N,N-dimethylformamide was added cesium carbonate (11 mg, 0.04 mmol) followed by allyl bromide (0.1 mL, 1.15 mmol). The resulting mixture was stirred at room temperature for 5 hours. Ether was added followed by water. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes:ethyl acetate) provided 2-[3-(allyloxy)phenyl]-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-8-amine (10 mg, 77%) as an oil. 1H NMR (CDCl3): δ 8.87 (broad, 1H), 8.01 (d, 1H), 7.30 (t, 1H), 7.20–7.17 (m, 2H), 6.95 (m, 1H), 6.78 (t, 1H), 6.38 (d, 1H), 6.28 (d, 1H), 6.03 (m, 1H), 30 5.43–5.24 (m, 4H), 4.54 (d, 2H), 4.34 (m, 1H), 3.91 (m, 1H), 2.12–2.04 (m, 4H), 1.82–1.55 (m, 12H); MS m/z 495 (M+1). This material was treated with anhydrous hydrochloric acid in ether to provide the corresponding hydrochoride salt as a yellow solid.

後処理

  1. washThe organic layer was washed with brine
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-3369ef6d311840b7a5b9b14ec8c9e975
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07186714B2

反応ノート

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