Ammonium Chloride → AM6545

HRID 532244

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HRID 532244 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 46912919AM6545수율 43.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 31268Pyrrolidine용매2회

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-88bceefa166843b9833a9897ebe786f2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853205B2

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