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

HRID 589366ノート

反応式

HRID 589366 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.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41](Cl)=[O:42].C(=O)(O)[O-].[Na+]>ClCCl>[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[C:41]([NH:1][C:2]1[CH:3]=[CH:4][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:22][CH:23]=1)=[O:42]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium BicarbonateHCID 89590263ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate

生成物 1

HCID 90449170ethyl 2-[1-[4-(2-naphthamido)benzyl]-1H-indazol-3-yl]acetate収率 46.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

The crude ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate (about 1.04 mmol) obtained in the last step and triethylamine (1.4 mL) were dissolved in dichloromethane (15 mL). In an ice bath, a dichloromethane solution (10 mL) of 2-naphthoyl chloride (210 mg, 1.1 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. It was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and filtered. The filtrate was removed under reduced pressure, and the resulting residue was chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a white solid 226 mg, at a total yield over two steps of reactions of 46.9%.

後処理

  1. additionUpon completion of the dropwise addition, it
  2. customwas reacted at room temperature for 16 hours
  3. customto quench
  4. extractionIt was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was removed under reduced pressure
  8. customthe resulting residue was chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-296059c26d1744d298597ef479efa3cf
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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