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

HRID 719508

反応式

HRID 719508 の反応式
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]3=[N:24][CH:25]=[N:26][C:27]([O:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[C:22]3[CH:21]=[N:20]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11].C(N(CC)CC)C.CN([CH:45]=[O:46])C>>[CH:1]1([O:7][C:45]([N:32]2[CH2:33][CH2:34][CH:29]([O:28][C:27]3[N:26]=[CH:25][N:24]=[C:23]4[N:19]([C:16]5[CH:17]=[CH:18][C:13]([S:10]([CH3:9])(=[O:11])=[O:12])=[CH:14][CH:15]=5)[N:20]=[CH:21][C:22]=34)[CH2:30][CH2:31]2)=[O:46])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 7966CyclohexanolHCID 8471TriethylamineHCID 218977741-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

生成物 1

HCID 218977224-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclohexyl ester

実験手順

Carbonyldiimidizole (0.28 mmol, 46 mg), and cyclohexanol (0.28 mmol, 34 μL) were dissolved in DMF (2 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride salt (0.16 mmol, 60 mg) and triethylamine (0.84 mmol, 118 μL) were added and continued to stir at 60° C. for 24 hours. The reaction mixture was quenched with water followed by an extraction with ethylacetate. Removal of organic solvents in vacuo and purification by HPLC provided compound A63 as a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.67 (s, 1H); 8.61 (d, 2H); 8.26 (s, 1H); 8.11 (d, 2H); 5.62 (h, 1H); 4.71 (h, 1H); 3.91 (m, 2H); 3.38 (m, 2H); 3.10 (s, 3H); 2.10 (m, 2H); 1.87 (m, 4H), 1.65 (m, 6H); 1.28 (m, 2H). LCMS (ESI), m/z 500.4 (MH+, 100%)

後処理

  1. stirringto stir at 60° C. for 24 hours
  2. customThe reaction mixture was quenched with water
  3. extractionfollowed by an extraction with ethylacetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by HPLC
  6. customprovided compound A63 as a white solid

出典と根拠

ORDレコード
ord-ee901c54ffaf48b2ba3f69238f83ffe6
出典データセット
uspto-grants-2006_11
特許番号
US07132426B2

関連ノート

読み込み中…