Sodium Hydroxide → 3-Cyano-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055724ノート

反応式

HRID 1055724 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:39])([F:38])([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29])#[N:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(#N)C.O>[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:38])([F:39])([F:35])([F:36])[F:37])[CH:33]=1)[C:28]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:29])#[N:24]

参加物

10

反応物 6

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896998123-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

生成物 1

HCID 896995363-Cyano-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

1.00 g (3.46 mmol) of the compound of Example 6A, 944 mg (3.46 mmol) of the compound of Example 23A and 1.58 g (4.15 mmol) of HATU were dissolved in 12.1 ml of anhydrous DMF, and 0.72 ml (4.15 mmol) of N,N-diisopropylethylamine was added. The reaction mixture was stirred at RT for 1 h and then stirred into 120 ml of 0.1 M aqueous sodium hydroxide solution. After a further 10 min of stirring at RT, the precipitate formed was filtered off and dried. This crude product was then separated into its components by preparative HPLC (Method 23). The product fractions were combined and concentrated to dryness on a rotary evaporator. The product obtained was suspended in a mixture of 10 ml of acetonitrile and 10 ml of water, made alkaline with a little saturated sodium bicarbonate solution and stirred at RT for 10 min. The solid was filtered off, washed with water and dried. This gave 1.12 g (69% of theory) of the title compound.

後処理

  1. stirringAfter a further 10 min of stirring at RT
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. customdried
  5. customThis crude product was then separated into its components by preparative HPLC (Method 23)
  6. concentrationconcentrated to dryness on a rotary evaporator
  7. customThe product obtained
  8. stirringstirred at RT for 10 min
  9. filtrationThe solid was filtered off
  10. washwashed with water
  11. customdried

出典と根拠

ORDレコード
ord-301c159b5f4d41ba99ba3ed94b190bb6
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

読み込み中…