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

HRID 1958428ノート

反応式

HRID 1958428 の反応式
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[C:15]3[CH:14]=[N:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH2:28]([O:30][C:31](Cl)=[O:32])[CH3:29].C(N(CC)CC)C>CN(C=O)C>[CH2:28]([O:30][C:31]([N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:20]2[N:19]=[CH:18][N:17]=[C:16]3[N:12]([C:9]4[CH:10]=[CH:11][C:6]([S:3]([CH3:2])(=[O:4])=[O:5])=[CH:7][CH:8]=4)[N:13]=[CH:14][C:15]=23)[CH2:23][CH2:24]1)=[O:32])[CH3:29]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 218977741-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

生成物 1

HCID 536304154-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid ethyl ester収率 18.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride salt (0.17 mmol, 70 mg), ethylchloroformate (0.25 mmol, 25 μL) and triethylamine (0.51 mmol, 72 μL) were dissolved in DMF (2 mL) and stirred for 60 minutes at room temperature. Progress of the reaction was monitored by TLC and LCMS. The reaction mixture was quenched with water. The product was extracted with ethyl acetate. Removal of organic solvents in vacuo and purification by HPLC provided compound A123 as a white solid (14 mg, 15%). Exact mass calculated for C20H23N5O5S 445.49, found 446.10 (MH+).

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionThe product was extracted with ethyl acetate
  3. customRemoval of organic solvents
  4. customin vacuo and purification by HPLC

出典と根拠

ORDレコード
ord-f8e348635a604c42b0cc84a3db43205e
出典データセット
uspto-grants-2013_04
特許番号
US08410119B2

反応ノート

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