Ethyl Acetate → N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide

HRID 456687

反応式

HRID 456687 の反応式
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:15]([N:16]=[CH:17][N:18]([CH3:20])[CH3:19])[C:10]2=[N:9][C:8]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O.Cl.[CH:30]1([NH:35][C:36]([NH2:38])=[NH:37])[CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH:30]1([NH:35][C:36]2[N:38]=[C:5]([C:7]3[N:11]4[CH:12]=[CH:13][CH:14]=[C:15]([N:16]=[CH:17][N:18]([CH3:20])[CH3:19])[C:10]4=[N:9][C:8]=3[C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH:4]=[CH:3][N:37]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69548821N'-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamideHCID 178479367HCID 178479367、化合物

生成物 1

HCID 69549491N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide収率 53.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of N′-[3-[(2E)-3-(dimethylamino)-2-propenoyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (130 mg, 0.34 mmol) in N,N-dimethylformamide was added N-cyclopentylguanidine hydrochloride (168 mg, 1.02 mmol), followed by anhydrous potassium carbonate (140 mg, 1.02 mmol). The resulting solution was heated at 100° C. for 16 hours. Upon cooling to room temperature, ethyl acetate and water were added. The phases were separated and the organics were washed with brine. The aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate) to give N′-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (80 mg, 53%) as a solid. 1H NMR (CDCl3): δ 9.09 (broad s, 1H), 8.60 (s, 1H), 8.04 (d, 1H), 7.63 (q, 2H), 7.04 (t, 2H), 6.78 (m, 2H), 6.36 (d, 1H), 5.14 (d, 1H), 4.31 (m, 1H), 3.10 (s, 3H), 3.05 (s, 3H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); MS m/z 444 (M+1).

後処理

  1. temperatureUpon cooling to room temperature
  2. customThe phases were separated
  3. washthe organics were washed with brine
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-f0cf492e05a94da5ac42f0506889884b
出典データセット
uspto-grants-2007_03
特許番号
US07186714B2

関連ノート

読み込み中…