Sodium Carbonate → HCID 57965001, 화합물

HRID 1931691노트

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HRID 1931691 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[C:31]3=[N:32][CH:33]=[N:34][C:35](Cl)=[C:30]3[CH:29]=[N:28]2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH2:23][CH:24]([N:27]2[C:31]3=[N:32][CH:33]=[N:34][C:35]([O:13][C:10]4[CH:11]=[CH:12][C:7]([C:4]5[N:3]=[C:2]([CH3:1])[O:6][N:5]=5)=[CH:8][CH:9]=4)=[C:30]3[CH:29]=[N:28]2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 49623974-(5-Methyl-1,2,4-oxadiazol-3-yl)phenolHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2회

생성물 1

HCID 57965001HCID 57965001, 화합물수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

A mixture of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenol (Enamine Ltd., Kiev, Ukraine; 32 mg, 0.178 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 60 mg, 0.178 mmol), and potassium carbonate (54 mg, 0.391 mmol) in dimethylformamide (1 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture, and the mixture was then filtered through a pad of silica gel to remove the precipitate. The silica gel pad was washed with methanol and the solvents were evaporated from the filtrate. The residue was purified by HPLC to afford 4-{4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyrazolo[3,4-d]pyrimidin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (17 mg, 20%) as an off white solid. Mass spectrum M+H-Boc=378.

후처리

  1. filtrationthe mixture was then filtered through a pad of silica gel
  2. customto remove the precipitate
  3. washThe silica gel pad was washed with methanol
  4. customthe solvents were evaporated from the filtrate
  5. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-87206d0af69140efbe8854599e2be0f9
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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