2-Amino-4-chloropyridine → 5-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide

HRID 2215584ノート

反応式

HRID 2215584 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.Cl.N1C=CC=CC=1.[C:16]1([NH:22][C:23]([N:25]2[C:33]3[C:28](=[CH:29][C:30]([NH2:34])=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCC1=O>[C:16]1([NH:22][C:23]([N:25]2[C:33]3[C:28](=[CH:29][C:30]([NH:34][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=4)=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)=[O:24])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 5818662-Amino-4-chloropyridineHCID 10176127Pyridinium chlorideHCID 210548515-Aminoindole-1-carboxylic acid phenylamide

生成物 1

HCID 210548085-(2-Aminopyridin-4-ylamino)indole-1-carboxylic acid phenylamide収率 104%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

2-Amino-4-chloropyridine (500 mg, 0.446 mmol) was dissolved in N-methylpyrrolidone (5.0 ml); pyridine hydrochloride (750 mg) and 5-aminoindole-1-carboxylic acid phenylamide (408 mg, 1.62 mmol) was added thereto; the reaction mixture was stirred at 100° C. for 6.5 hours. After cooling to room temperature, the reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate; the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system). The obtained pale yellow oil was solidified with diethyl ether; and the crystals were suspended in diethyl ether, filtered off, washed with diethyl ether, and dried to yield the title compound (188 mg, 0.464 mmol, 35.7%) as pale yellow crystals.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system)
  7. filtrationfiltered off
  8. washwashed with diethyl ether
  9. customdried

出典と根拠

ORDレコード
ord-2f77bc06fa03476a836480ab33933d17
出典データセット
uspto-grants-2006_09
特許番号
US07109219B2

反応ノート

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