Water → [1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide

HRID 1247808ノート

反応式

HRID 1247808 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][CH:9]=[O:10].[C:11](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:7][N:6]1[C:2]([NH:1][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:3]([NH:8][CH:9]=[O:10])[CH:4]=[N:5]1

参加物

7

反応物 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 21904554N-(5-Amino-1-methyl-1H-pyrazol-4-yl)formamide

生成物 1

HCID 21904512[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide収率 52.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

The crude product of N-(5-amino-1-methyl-1H-pyrazol-4-yl)formamide (13.33 g) was dissolved in N,N-dimethylformamide (130 ml). To the solution were added trityl chloride (29.2 g), triethylamine (66.3 ml) and 4-dimethylaminopyridine (465 mg), and the mixture was stirred at 60° C. for 5 hours. To the reaction mixture was added water, and the whole mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a white solid. The solid was triturated with ethyl acetate/diisopropyl ether (1:1) to give N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide (19.18 g). The NMR spectrum of this compound indicates the existence of its rotamer.

後処理

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a white solid
  6. customThe solid was triturated with ethyl acetate/diisopropyl ether (1:1)

出典と根拠

ORDレコード
ord-00042078e6d34b3eb8c53b1975e753ae
出典データセット
uspto-grants-2006_10
特許番号
US07129232B2

反応ノート

読み込み中…