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

HRID 456688노트

반응식

HRID 456688 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9923aa4810594f5fa5bf731c8035a638
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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