Acetonitrile → Etravirine

HRID 243543

反応式

HRID 243543 の反応式
C(#N)C.[Br:4][C:5]1[C:6]([NH:31]C(=O)C2C=CC=CC=2)=[N:7][C:8]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)=[N:9][C:10]=1[O:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([C:19]#[N:20])=[CH:14][C:13]=1[CH3:21].O.[OH-].[Li+]>CC(O)C>[CH3:18][C:17]1[CH:16]=[C:15]([C:19]#[N:20])[CH:14]=[C:13]([CH3:21])[C:12]=1[O:11][C:10]1[N:9]=[C:8]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[N:7]=[C:6]([NH2:31])[C:5]=1[Br:4]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 168937Lithium hydroxide, monohydrateHCID 70978955N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]benzamide

生成物 1

HCID 193962Etravirine

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
59 °C

実験手順

1350 ml of acetonitrile was taken into a RB flask at 27±3° C. To this was added 900 ml of IPA. To the reaction mixture 150 g of N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]benzamide and 35.2 g of lithium hydroxide monohydrate were added and heated to 59±3° C. The reaction mixture was maintained at the same temperature for 10 hrs. After completion of the reaction, the reaction mixture was cooled to 47±3° C. and filtered. The solid was washed with acetonitrile and suck dried. The wet cake was taken into another flask to which was added 1500 ml of water, stirred for 30 mins and filtered to obtain the solid. The solid was washed with water and dried under vacuum at 73±3° C. to isolate Etravirine.

後処理

  1. customwas taken into a RB flask at 27±3° C
  2. temperatureThe reaction mixture was maintained at the same temperature for 10 hrs
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to 47±3° C.
  5. filtrationfiltered
  6. washThe solid was washed with acetonitrile and suck
  7. customdried
  8. customThe wet cake was taken into another flask to which
  9. additionwas added 1500 ml of water
  10. filtrationfiltered
  11. customto obtain the solid
  12. washThe solid was washed with water
  13. customdried under vacuum at 73±3° C.

出典と根拠

ORDレコード
ord-91e5b7c5f356461e878247d8e5899502
出典データセット
uspto-grants-2014_02
特許番号
US08653266B2

関連ノート

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