Dimethylformamide → 5-(5-Chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 2037042ノート

反応式

HRID 2037042 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][CH:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[CH3:18])[N:12]3[N:25]=[CH:26][CH:27]=[C:11]3[N:10]=2)[CH:7]=1.P(Cl)(Cl)(Cl)=O.CN([CH:37]=[O:38])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][CH:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[CH3:18])[N:12]3[N:25]=[CH:26][C:27]([CH:37]=[O:38])=[C:11]3[N:10]=2)[CH:7]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 58314469HCID 58314469、化合物

生成物 1

HCID 583140035-(5-Chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde収率 41%

実験手順

In a reaction flask, N5-(5-chloro-2-fluorophenyl)-N7-(2-morpholinopropyl)pyrazolo[1,5-a]pyrimidine-5,7-diamine (84 mg, 0.21 mmol) was dissolved in DMF (0.9 mL) then phosphorous oxychloride (58 uL, 0.62 mmol) was added slowly at room temperature. The reaction mixture was allowed to stir at room temperature for 2 days then quenched by addition to 6N NaOH solution. The pH of the mixture was adjusted with 6N HCl to pH=7-9. The solid was recovered by filtration and washed with water. The product, 5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was purified by preparative TLC (5% acetone/dichloromethane) to yield 37 mg of the desired product (41% yield). LCMS (M+1=433)

後処理

  1. customthen quenched by addition to 6N NaOH solution
  2. filtrationThe solid was recovered by filtration
  3. washwashed with water
  4. customThe product, 5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was purified by preparative TLC (5% acetone/dichloromethane)

出典と根拠

ORDレコード
ord-fe85ac5b30654090b59730985b14be45
出典データセット
uspto-grants-2013_11
特許番号
US08575177B2

反応ノート

読み込み中…