Methyl chloroformate → Vericiguat Impurity 100

HRID 1875457ノート

反応式

HRID 1875457 の反応式
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[C:16]([NH2:22])[N:15]=2)[N:6]=1.Cl[C:28]([O:30][CH3:31])=[O:29]>N1C=CC=CC=1>[CH3:31][O:30][C:28](=[O:29])[NH:21][C:17]1[C:16]([NH2:22])=[N:15][C:14]([N:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[C:5]([CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[F:1])=[N:6]2)=[N:19][C:18]=1[NH2:20]

参加物

4

反応物 2

HCID 6586Methyl chloroformateHCID 24794429HCID 24794429、化合物

生成物 1

HCID 24794430Vericiguat Impurity 100

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

200 mg (0.57 mmol) of 2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine from example 8 are dissolved in 10 ml of pyridine. The solution is cooled to 0° C., and 81 mg (0.86 mmol) of methyl chloroformate are added. The reaction mixture is stirred at RT overnight and then concentrated in vacuo, mixed with ethyl acetate and washed twice with water and with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is purified by preparative HPLC to result in 125 mg (54% of theory) of the title compound as a pale beige solid.

後処理

  1. concentrationconcentrated in vacuo
  2. additionmixed with ethyl acetate
  3. washwashed twice with water and with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-d6e0e2c53cee4919a0bfd3950ffb96ee
出典データセット
uspto-grants-2012_11
特許番号
US08309551B2

反応ノート

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