2-Chloroaniline → HCID 24771611, 화합물

HRID 645363노트

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HRID 645363 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ONN1C=CN=N1.C(N(CC)C(C)C)(C)C.[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59](O)=[O:60])[N:58]=2)[CH:55]=1>CN(C)C=O.C(=O)([O-])O.[Na+]>[Cl:49][C:50]1[CH:51]=[CH:52][C:53]2[N:54]([CH:56]=[C:57]([C:59]([NH:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[Cl:1])=[O:60])[N:58]=2)[CH:55]=1

참가 물질

8

반응물 5

HCID 72402-ChloroanilineHCID 81531DiisopropylethylamineHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136346319HCID 136346319, 화합물

생성물 1

HCID 24771611HCID 24771611, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

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온도
70 °C

실험 절차

54 μl of 2-chloroaniline, 211 mg of HATU, 75 mg of 1-hydroxyaminotriazole and 237 μl of N,N-diisopropylethylamine are added to a solution of 100 mg of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 1 ml of N,N-dimethylformamide. The reaction mixture is heated at 70° C. for 16 hours, diluted with a saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. The residue is purified by flash chromatography on silica, elution being carried out with a hexane/ethyl acetate 70/30 mixture to give 62 mg of 6-chloro-N-(2-chlorophenyl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. customThe combined organic phases are dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash chromatography on silica, elution

출처 및 근거

ORD 기록
ord-e642ba07940644169aad1ad2344d58f2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704989B2

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