Ammonium Chloride → AM6545

HRID 532244

反応式

HRID 532244 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)=[C:12]([CH3:21])[C:11]([C:22]([NH:24][N:25]2[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]2)=[O:23])=[N:10]1.[C:33]([CH2:35][CH2:36][C:37]#[CH:38])#[N:34].[Cl-].[NH4+]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:33]([CH2:35][CH2:36][C:37]#[C:38][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]=[C:11]([C:22]([NH:24][N:25]3[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]3)=[O:23])[C:12]=2[CH3:21])=[CH:15][CH:16]=1)#[N:34]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 1405604-Cyano-1-butyneHCID 469129201-(2,4-dichlorophenyl)-4-methyl-5-(4-iodophenyl)-N-(1,1-dioxothiomorpholino)-1H-pyrazole-3-carboxamide

生成物 1

HCID 46912919AM6545収率 43.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 31268Pyrrolidine溶媒2 回

実験手順

To a stirred solution of amide obtained from step E (2 g, 3.3 mmol) in pyrrolidine (40 ml), under an argon atmosphere, tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.3 mmol) was added. The reaction mixture was stirred for 5 min at room temperature, and subsequently 4-cyano-1-butyne (0.78 g, 9.9 mmol) in pyrrolidine (1.5 ml) was added over 5 minutes. The resulting mixture was heated at 80-85° C. for 10 h. The reaction was hydrolyzed with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic extract was dried over MgSO4 and the solvent was removed in vacuo. Purification by flash column chromatography on silica gel (eluant ethylacetate) gave compound 15 as a white solid (0.8 g, 43.7%)

後処理

  1. temperatureThe resulting mixture was heated at 80-85° C. for 10 h
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography on silica gel (eluant ethylacetate)

出典と根拠

ORDレコード
ord-88bceefa166843b9833a9897ebe786f2
出典データセット
uspto-grants-2014_10
特許番号
US08853205B2

関連ノート

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