Triethylamine → ethyl 2-[1-[4-(6-methylnicotinamido)benzyl]-1H-indazol-3-yl]acetate

HRID 589398ノート

反応式

HRID 589398 の反応式
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][N:33]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]3)=[CH:22][CH:23]=2)=[O:37])=[CH:34][N:33]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 218904586-Methylnicotinoyl chlorideHCID 89590263ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate

生成物 1

HCID 89590264ethyl 2-[1-[4-(6-methylnicotinamido)benzyl]-1H-indazol-3-yl]acetate収率 72.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate (258 mg, 0.83 mmol) and triethylamine (0.4 mL, 2.87 mmol) were dissolved in dichloromethane (15 mL), and in an ice bath, dichloromethane solution (10 mL) of the prepared 6-methylnicotinoyl chloride (about 1.00 mmol) was added dropwise slowly. Upon completion of the dropwise addition, it was reacted at room temperature for 16 hours. An aqueous solution of sodium bicarbonate was added to quench, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduce pressure, and chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a white solid 258 mg, at a yield of 72.3%.

後処理

  1. additionUpon completion of the dropwise addition, it
  2. customwas reacted at room temperature for 16 hours
  3. customto quench
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-5666e46ff67c4423bf9b6c10c3acbb4c
出典データセット
uspto-grants-2016_01
特許番号
US09233098B2

反応ノート

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