Ethylenediamine → 2-[(2-methanesulfonyl-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide

HRID 1434698ノート

反応式

HRID 1434698 の反応式
Br[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1.[CH3:29][S:30](N)(=[O:32])=[O:31].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(N)C[NH2:44]>O.[Cu]I.O1CCOCC1>[CH3:29][S:30]([C:2]1[CH:7]=[C:6]([CH:8]([NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])[NH2:44])[CH:5]=[CH:4][N:3]=1)(=[O:32])=[O:31]

参加物

8

反応物 4

HCID 3301EthylenediamineHCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 103437292-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide

生成物 1

HCID 688212462-[(2-methanesulfonyl-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide収率 258.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

90 mg (0.2 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide and 23 mg (0.24 mmol) of methanesulfonic acid amide are introduced into 5 ml of dioxane and mixed in succession with 4 mg (0.02 mmol) of copper(I) iodide, 85 mg (0.4 mmol) of potassium phosphate and 2 mg (0.02 mmol) of ethylenediamine. After 1 hour of stirring at a bath temperature of 120° C., it is diluted with 20 ml of water and concentrated by evaporation. It is then made alkaline with ammonia and shaken out three times with 25 ml each of ethyl acetate. The collected organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is made crystalline with ethyl acetate and a little hexane, stirred and suctioned off. 24 mg (26% of theory) of 2-[(2-methanesulfonyl-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide with a melting point of 214.5° C. is obtained.

後処理

  1. concentrationconcentrated by evaporation
  2. stirringshaken out three times with 25 ml each of ethyl acetate
  3. washThe collected organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. stirringa little hexane, stirred

出典と根拠

ORDレコード
ord-d76da8f6df274a0e873da3c3265dd3b5
出典データセット
uspto-grants-2009_11
特許番号
US07615565B2

反応ノート

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