Sodium ethoxide → 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 724007

반응식

HRID 724007 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[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:24]([C:25](=O)[C:26]#[CH:27])=[C:18]2[CH:17]=1>C(O)C>[Cl:15][C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[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:18]2[CH:17]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 221809211-[5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, 화합물

생성물 1

HCID 102238594-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine수율 66.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium ethylate (0.7 mL (2.09 mmol), 210% in ethanol) and cyclopentyl guanidine hydrochloride (0.47 g, 2.88 mmol) were added sequentially to ethanol (30 mL). The resulting solution was stirred at room temperature for 30 minutes. 1-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-propyn-1-one (0.5 g, 1.61 mmol) was added, and the suspension was stirred at room temperature for 2 days. The reaction was quenched by the addition of water. The aqueous phase was extracted by ethyl acetate. The organics were combined, washed with brine and dried over magnesium sulfate. Filtration and concentration gave a solid. This solid was recrystallized from methanol to give 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.45 g, 66%) as a pale yellow solid. 1H NMR (CDCl3) δ 8.59 (b, 1H), 8.42 (d, 1H), 8.05 (d, 1H), 7.59 (d, 2H), 7.03 (d, 2H), 6.91 (dd, 1H), 6.39 (d, 1H), 5.34 (broad s, 1H), 4.42 (m, 1H), 3.92 (s, 3H), 2.17 (m, 2H), 1.86–1.60 (m, 6H); MS m/z 420 (M+1).

후처리

  1. stirringthe suspension was stirred at room temperature for 2 days
  2. customThe reaction was quenched by the addition of water
  3. extractionThe aqueous phase was extracted by ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration
  7. customgave a solid
  8. customThis solid was recrystallized from methanol

출처 및 근거

ORD 기록
ord-a65ee26c3d8f484dbd82136678d4d9d7
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141569B2

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