Sodium Bicarbonate → HCID 86652268, 화합물

HRID 1256286노트

반응식

HRID 1256286 반응식
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][CH:20]2[C:22](Cl)=[O:23])=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:22]([C@@H:20]2[CH2:21][C@H:19]2[C:16]2[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=2)=[O:23])[CH:3]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amineHCID 767027172-(Pyridin-4-yl)cyclopropanecarbonyl chloride

생성물 1

HCID 86652268HCID 86652268, 화합물수율 62.1%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

In a 100 mL round-bottomed flask was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 2.74 g, 15.02 mmol) in pyridine (75 ml) to give a yellow solution. Then, at 0° C., 2-(pyridin-4-yl)cyclopropanecarbonyl chloride (7D, 0.19 g, 1.046 mmol) in pyridine (1 ml) was added to give a suspension. After the reaction was complete, saturated NaHCO3 solution was added and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica using 20% MeOH/CH2Cl2 to provide trans-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide (7E, 213 mg, 4% for 3 steps) as a yellow solid. 1H NMR (DMSO-d6) δ: 11.43 (s, 1H), 8.46 (d, J=6.1 Hz, 2H), 7.97 (s, 1H), 7.15-7.27 (m, 2H), 6.40 (s, 1H), 2.39-2.46 (m, 4H), 2.28-2.35 (m, 1H), 1.46-1.67 (m, 2H). ESI-MS: m/z 328.0 (M+H)+.

후처리

  1. customto give a yellow solution
  2. customto give a suspension
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica using 20% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-f973b237c91845e88ba26719d4125a06
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461163B2

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