N,N'-Dimethylethylenediamine → HCID 178513489、化合物

HRID 64333

反応式

HRID 64333 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2Br)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[C:3]=1[C:30]([NH2:32])=[O:31].CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[N+:13]([C:11]1[CH:10]=[CH:9][C:8]2[NH:1][C:2]3[N:6]([N:5]=[C:4]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:19][CH:18]=4)[C:3]=3[C:30]([NH2:32])=[O:31])[C:7]=2[CH:12]=1)([O-:15])=[O:14]

参加物

6

反応物 3

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 1176682335-Amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide

生成物 1

HCID 178513489HCID 178513489、化合物収率 52%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-amino-1-(2-bromo-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (149 mg, 0.3 mmol, crude), CuI (5.7 mg, 0.03 mmol), N1,N2-dimethylethane-1,2-diamine (3 mg, 0.03 mmol), K3PO4 (64 mg, 0.3 mol) in 15 mL of DMF was stirred at 60° C. under N2 for 5 hr, until TLC analysis showed that most of starting material was consumed. The reaction was cooled to RT. The solvent was removed under reduced pressure. The residue was chromatographed on 5 g of silica gel using DCM/MeOH (200/1 to 20/1) to afford 62 mg (52%) of 7-nitro-2-(4-phenoxyphenyl)-4H-benzo[4,5]imidazo[1,2-b]pyrazole-3-carboxamide as a tan solid. MS (ESI) m/e [M+1]+ 414.

後処理

  1. customwas consumed
  2. temperatureThe reaction was cooled to RT
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was chromatographed on 5 g of silica gel

出典と根拠

ORDレコード
ord-0f8b7e8bbaa3476090c8dfdeb1cd92e4
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

関連ノート

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