Sodium Carbonate → 7-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide

HRID 2364762ノート

反応式

HRID 2364762 の反応式
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:26]([OH:28])=O)=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C:7]2([CH2:33][CH3:34])[CH2:31][CH3:32])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:40]1(OC(N(C)C)=[N+](C)C)[C:44]2[CH:45]=[CH:46]C=[CH:48][C:43]=2N=N1.[CH:57]([N:60](C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:26]([NH:40][CH:44]5[CH2:43][CH2:48][N:60]([CH3:57])[CH2:46][CH2:45]5)=[O:28])=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C:7]2([CH2:31][CH3:32])[CH2:33][CH3:34])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 681073747-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid

生成物 1

HCID 510367897-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide収率 16.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7-[(8-Cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-2,3-dihydrobenzofuran-4-carboxylic acid 42b (50 mg, 0.11 mmol) was dissolved in 20 mL of dichloromethane followed by the addition of O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (35 mg, 0.11 mmol), diisopropylethylamine (31 mg, 0.24 mmol) and 1-methyl-piperidyl-4-yl-amine (13 mg, 0.11 mmol) successively. The reaction solution was stirred at room temperature for 1 hour. The resulting solution was added with 50 mL of saturated sodium carbonate solution and extracted with dichloromethane (100 mL×2). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound 7-[(8-cyclopentyl-7,7-diethyl-5-methyl-6-oxo-pteridin-2-yl)amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 42 (10 mg, yield: 16.0%) as a white solid.

後処理

  1. extractionextracted with dichloromethane (100 mL×2)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system

出典と根拠

ORDレコード
ord-c6c1a5623d5644879bf453015349fe9b
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

読み込み中…