Acetonitrile → 2-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide

HRID 2387216

반응식

HRID 2387216 반응식
[NH2:1][C:2]1[N:13]=[CH:12][C:11](Br)=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[CH:15]1([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=2)(=[O:21])=[O:20])[CH2:17][CH2:16]1.C(Cl)Cl.CC#N>C([O-])([O-])=O.[Na+].[Na+].COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:13]=[CH:12][C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([S:19](=[O:20])(=[O:21])[NH:18][CH:15]3[CH2:16][CH2:17]3)[CH:23]=2)=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

참가 물질

9

반응물 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 44119335(3-(N-Cyclopropylsulfamoyl)phenyl)boronic acidHCID 596997242-amino-5-bromo-N-methoxy-N-methylnicotinamide

생성물 1

HCID 866345442-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

실험 절차

A suspension of 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide (0.2 g, 0.77 mmol), N-cyclopropyl 3-boronobenzenesulfonamide (0.2 g, 0.84 mmol), Pd(dppf)Cl2.DCM (0.063 g, 0.077 mmol) in 2M Na2CO3 (1 ml) and DME (3 ml) is heated at reflux for 1 hour. The crude reaction mixture is subjected to column chromatography (Isolute™ C18, 0-100% MeCN in water −0.1% TFA). All the acetonitrile is removed in vacuo, and the aqueous solution remaining is adjusted to basic pH using NaHCO3. The product is extracted into DCM, and dried (MgSO4). Concentration and drying in vacuo at 40° C. yields the title compound. [M+H]+ 726

후처리

  1. temperatureat reflux for 1 hour
  2. customThe crude reaction mixture
  3. customAll the acetonitrile is removed in vacuo
  4. extractionThe product is extracted into DCM
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customdrying in vacuo at 40° C.

출처 및 근거

ORD 기록
ord-0f769ef43d8646fbb8191300db62f2a9
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268834B2

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