Sodium Hydroxide → 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine

HRID 456688ノート

反応式

HRID 456688 の反応式
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([N:22]=CN(C)C)[C:16]4=[N:15][C:14]=3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH2:22])[C:16]4=[N:15][C:14]=3[C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 69549491N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide

生成物 1

HCID 101783513-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine収率 88.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

N′-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (70 mg, 0.16 mmol) was dissoved in methanol. To this solution was added 1N aqueous sodium hydroxide and the resulting mixture heated at reflux for 6 hours. The resulting mixture was concentrated in vacuo followed by addition of ethyl acetate and water. The phases were separated and the ethyl acetate phase dried (magnesium sulfate), filtered and concentrated. The resulting solid was purified by silica gel chromatography (ethyl acetate) to give 55 mg (88%) of 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-amine as a solid. 1H NMR (CDCl3): δ 8.97 (d, 1H), 8.12 (d, 1H), 7.68 (q, 2H), 7.15 (t, 2H), 6.78 (t, 1H), 6.54 (d, 1H), 6.41 (d, 1H), 5.24 (d, 1H), 4.60 (s, 2H), 4.40 (m, 1H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); 19F NMR (CDCl3) δ −113.7; MS m/z 389 (M+1).

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. additionfollowed by addition of ethyl acetate and water
  5. customThe phases were separated
  6. dry with materialthe ethyl acetate phase dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was purified by silica gel chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-9923aa4810594f5fa5bf731c8035a638
出典データセット
uspto-grants-2007_03
特許番号
US07186714B2

反応ノート

読み込み中…