Methyl chloroformate → Methyl {4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methylpyrimidin-5-yl}carbamate formate

HRID 510056ノート

反応式

HRID 510056 の反応式
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[C:16]([CH3:22])[N:15]=2)=[N:6]1.Cl[C:28]([O:30][CH3:31])=[O:29]>N1C=CC=CC=1.ClCCl>[CH:28]([OH:30])=[O:29].[NH2:20][C:18]1[C:17]([NH:21][C:28](=[O:29])[O:30][CH3:31])=[C:16]([CH3:22])[N:15]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[F:1])[N:6]=2)[N:19]=1

参加物

5

反応物 2

HCID 6586Methyl chloroformate3 回HCID 582869932-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methylpyrimidine-4,5-diamine

生成物 1

HCID 86720046Methyl {4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methylpyrimidin-5-yl}carbamate formate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

150 mg (0.343 mmol) of the compound from example 54A were initially charged in pyridine (3 ml) under argon and cooled to 0° C. Subsequently, a solution of 27 μl (0.34 mmol) of methyl chloroformate in dichloromethane (1 ml) was added dropwise, and the mixture was brought to RT and stirred overnight. Then the mixture was cooled again to 0° C., then 5 μl of methyl chloroformate (dissolved in 0.5 ml of dichloromethane) were added and the mixture was stirred at RT for a further 30 min. Subsequently, another 5 μl of methyl chloroformate (dissolved in 0.5 ml of dichloromethane) were added at 0° C. and the mixture was stirred at RT overnight. The reaction mixture was brought to RT and concentrated by rotary evaporation. The residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 113 mg (71% of theory) of the title compound in solid form.

後処理

  1. customwas brought to RT
  2. temperatureThen the mixture was cooled again to 0° C.
  3. stirringthe mixture was stirred at RT for a further 30 min
  4. stirringthe mixture was stirred at RT overnight
  5. customwas brought to RT
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient)
  8. concentrationthe product fractions were concentrated

出典と根拠

ORDレコード
ord-431671aecd7040cbbc61924bd07f2819
出典データセット
uspto-grants-2015_08
特許番号
US09096592B2

反応ノート

読み込み中…