2-Ethyl-1-butanol → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl ester

HRID 719460ノート

反応式

HRID 719460 の反応式
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][OH:17])[CH3:14].[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]3=[N:35][CH:36]=[N:37][C:38]([O:39][CH:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)=[C:33]3[CH:32]=[N:31]2)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(N(CC)CC)C>CS(C)=O>[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16][O:17][C:6]([N:43]1[CH2:44][CH2:45][CH:40]([O:39][C:38]2[N:37]=[CH:36][N:35]=[C:34]3[N:30]([C:27]4[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=4)[N:31]=[CH:32][C:33]=23)[CH2:41][CH2:42]1)=[O:7])[CH3:14]

参加物

6

反応物 4

HCID 73582-Ethyl-1-butanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

生成物 1

HCID 218977034-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid 2-ethyl-butyl ester収率 44.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and 2-ethyl-butan-1-ol (0.51 mmol, 52 mg) were dissolved in DMSO (1 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.17 mmol, 70 mg) and triethylamine (0.51 mmol, 72 μL) were added and heated in a microwave at 120° C. for 6 minutes. The progress of the reaction was monitored by LCMS. The reaction mixture was quenched with water and the product was extracted with ethylacetate. Removal of organic solvents in vacuo and purification by HPLC provided Compound A119 as a white solid (38 mg, 36%). Exact mass calculated for C24H31N5O5S 501.60, found 502.3 (MH+).

後処理

  1. temperatureheated in a microwave at 120° C. for 6 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionthe product was extracted with ethylacetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by HPLC

出典と根拠

ORDレコード
ord-89c331719dde4464972e7a8cac56a284
出典データセット
uspto-grants-2006_11
特許番号
US07132426B2

反応ノート

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