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Sodium ethoxide → 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 1269069
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HRID 1269069 반응식
CC[O-].[Na+].Cl.[CH:6]1([NH:11][C:12]([NH2:14])=[NH:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:15][C:16]1[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:24]([C:25](=O)[C:26]#[CH:27])=[C:20]2[CH:19]=[CH:18][CH:17]=1>C(O)C>[Cl:15][C:16]1[N:21]2[N:22]=[C:23]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])[C:24]([C:25]3[CH:26]=[CH:27][N:14]=[C:12]([NH:11][CH:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)[N:13]=3)=[C:20]2[CH:19]=[CH:18][CH:17]=1
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참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 184465971-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, 화합물

생성물 1

HCID 111768674-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine수율 65%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium ethylate solution (21% T, 0.5 mL, 1.43 mmol) was added to ethanol followed by cyclopentylguanidine hydrochloride (323 mg, 1.98 mmol). The mixture was stirred at room temperature for 30 minutes. 1-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (313 mg, 1.10 mmol) was added to the resultant solution and stirred at room temperature for 15 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue. The phases were separated, the organic phase dried (magnesium sulfate), filtered and concentrated. The residue was recrystallized from ethyl acetate. 4-[7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (280 mg, 65%) was obtained as a yellow solid. 1H-NMR (CDCl3): δ 8.50 (d, 1H), 8.15 (d, 1H), 7.49 (d, 1H), 7.27 (t, 1H), 7.06 (d, 1H), 6.41 (d, 1H), 6.36 (d, 1H), 5.10 (d, 1H), 4.35 (m, 1H), 2.12 (s, 3H), 2.08 (m, 2H), 1.78–1.53 (m, 6H). MS m/z 394 (M+1).

후처리

  1. stirringstirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionEthyl acetate and water were added to the residue
  4. customThe phases were separated
  5. dry with materialthe organic phase dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-2dca8a713af54b93ae23f86125a1076a
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07199120B2

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