Sodium Carbonate → HCID 57965012, 화합물

HRID 1931596노트

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HRID 1931596 반응식
[CH:1]([C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH:12]([NH:15][NH2:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:17][C:18]1[C:23]([CH:24]=O)=[C:22](Cl)[N:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:17][C:18]1[N:19]=[CH:20][N:21]=[C:22]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:10][CH2:11]3)[N:16]=[CH:24][C:23]=12

참가 물질

5

반응물 3

HCID 10340Sodium Carbonate2회HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde2회HCID 57964979HCID 57964979, 화합물2회

생성물 1

HCID 57965012HCID 57965012, 화합물수율 36%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
140 °C

실험 절차

A mixture of [4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-hydrazine (Intermediate 12; 230 mg, 1.0 mmol), 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16; 182 mg, 1.0 mmol) and sodium carbonate (218 mg, 2.1 mmol) in acetonitrile was heated in the microwave at 140° C. for 10 min. Saturated aqueous sodium carbonate was added and the reaction mixture was filtered. The filtrate was extracted with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 10% ethyl acetate/hexanes to give 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (125 mg, 35%) as a white solid. Mass spectrum M+=346.

후처리

  1. filtrationthe reaction mixture was filtered
  2. extractionThe filtrate was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography
  7. washeluting with 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-0fdd78d6ab674a2dbd81a5c03cbed1c8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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