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

HRID 2387216

反応式

HRID 2387216 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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

後処理

  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.

出典と根拠

ORDレコード
ord-0f769ef43d8646fbb8191300db62f2a9
出典データセット
uspto-grants-2012_09
特許番号
US08268834B2

関連ノート

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