Sodium Carbonate → HCID 57965001、化合物

HRID 1931691ノート

反応式

HRID 1931691 の反応式
[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]

参加物

6

反応物 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-carboxylate2 回

生成物 1

HCID 57965001HCID 57965001、化合物収率 20%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-87206d0af69140efbe8854599e2be0f9
出典データセット
uspto-grants-2012_05
特許番号
US08188098B2

反応ノート

読み込み中…