Diethyl Ether → 3-(2-anilinopyrimidin-4-yl)-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 896770

反応式

HRID 896770 の反応式
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:15]([C:16](=O)/[CH:17]=[CH:18]/N(C)C)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+]([O-])([O-])=O.[C:34]1([NH:40][C:41]([NH2:43])=[NH2+:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C)C=O.O>[NH:40]([C:41]1[N:43]=[C:16]([C:15]2[C:14]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)=[N:13][N:12]3[C:7]([NH:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:8][CH:9]=[CH:10][C:11]=23)[CH:17]=[CH:18][N:42]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 11372773(2E)-1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-oneHCID 178418786HCID 178418786、化合物

生成物 1

HCID 52757013-(2-anilinopyrimidin-4-yl)-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a solution of (2E)-1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (100 mg, 0.25 mmol) in N,N-dimethylformamide (5 mL) was added N-phenylguanidinium nitrate (252 mg, 1.27 mmol) and potassium carbonate (175 mg, 1.27 mmol). The suspension was heated at 140° C. (bath temperature) for 21 hours. The mixture was cooled to room temperature, 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 3-(2-anilino-4-pyrimidinyl)-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine which was recrystallized from ether/hexanes (90 mg, 76%) to give a white crystalline solid. 1H NMR (CDCl3): δ 8.15 (d. 1 H), 7.69-7.59 (m, 5 H), 7.32-7.27 (m, 3 H), 7.18-7.13 (m, 3 H), 7.02 (t, 1 H), 6.49 (d, 1 H), 6.06-6.01 (m, 2 H), 4.01 (m, 1 H), 2.20-2.10 (m, 2 H), 1.86-1.64 (m, 6 H); 13C NMR (CDCl3): δ 163.20 (d, JCF=246.6 Hz), 161.55, 160.11, 156.76, 152.27, 142.72, 141.15, 139.74, 131.47 (d, JCF=8.3 Hz), 129.72 (d, JCF=3.4 Hz), 128.82, 128.66, 122.28, 119.52, 115.60 (d, JCF=21.3 Hz), 110.83, 106.91, 105.15, 90.34, 53.86, 33.32, 24.05; MS m/z 465 (M+1).

後処理

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

出典と根拠

ORDレコード
ord-6509dd48a10d4d76b7132da7949ddc1e
出典データセット
uspto-grants-2005_07
特許番号
US06919352B2

関連ノート

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