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

HRID 1528678ノート

反応式

HRID 1528678 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=3)[N:9]=[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:5]2=[N:6][CH:7]=1.Cl[C:29]([O:31][CH3:32])=[O:30]>N1C=CC=CC=1>[NH2:19][C:13]1[C:14]([NH:18][C:29](=[O:30])[O:31][CH3:32])=[C:15]([NH2:17])[N:16]=[C:11]([N:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[N:9]2)[N:12]=1

参加物

4

反応物 2

HCID 6586Methyl chloroformateHCID 675168882-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine

生成物 1

HCID 56963347Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

Under argon, 1.00 g (2.72 mmol) of the compound from example 8A was initially charged in pyridine (55 ml), the mixture was cooled to 0° C. and 228 μl (2.72 mmol) of methyl chloroformate (solution in 10 ml of dichloromethane) were then added dropwise. The reaction mixture was stirred further at RT overnight and then concentrated. The residue was triturated with ethanol and the solid was filtered off and dried at 50° C. under high vacuum. This gave 873 mg (75% of theory) of the target compound as a solid. The filtrate was re-concentrated, and preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient) of the residue gave a further 180 mg (16% of theory) of the target compound.

後処理

  1. concentrationconcentrated
  2. customThe residue was triturated with ethanol
  3. filtrationthe solid was filtered off
  4. customdried at 50° C. under high vacuum
  5. concentrationThe filtrate was re-concentrated
  6. custompreparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient) of the residue gave a further 180 mg (16% of theory) of the target compound

出典と根拠

ORDレコード
ord-93d00c0099c14445b13de192246ab607
出典データセット
uspto-grants-2015_07
特許番号
US09090609B2

反応ノート

読み込み中…