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

HRID 1055672ノート

反応式

HRID 1055672 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.[CH: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])=[O: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.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH:28]([C:27]1[CH:26]=[C:25]([CH:33]=[C:32]([S:34]([F:38])([F:39])([F:35])([F:36])[F:37])[CH:31]=1)[C:23]([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:24])=[O:29]

参加物

7

反応物 5

HCID 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 896999913-Formyl-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 897000213-Formyl-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 1

HCID 6228Dimethylformamide溶媒

実験手順

320 mg (1.11 mmol) of the compound of Example 6A, 336 mg (1.22 mmol) of the compound of Example 36A and 504 mg (1.33 mmol) of HATU were dissolved in 3.3 ml of DMF, 0.23 ml (1.33 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 3 h. The reaction was then stirred into 30 ml of semiconcentrated aqueous sodium bicarbonate solution. After 10 min of stirring at RT, the precipitate formed was filtered off, washed with water and dried. The crude product obtained in this manner was purified by preparative HPLC (Method 12). The product fractions were concentrated, the residue was dissolved in ethyl acetate and the mixture was washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue gave 100 mg (16% of theory) of the title compound.

後処理

  1. stirringAfter 10 min of stirring at RT
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried
  6. customThe crude product obtained in this manner
  7. customwas purified by preparative HPLC (Method 12)
  8. concentrationThe product fractions were concentrated
  9. dissolutionthe residue was dissolved in ethyl acetate
  10. washthe mixture was washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  11. dry with materialThe organic phase was dried over sodium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customDrying of the residue

出典と根拠

ORDレコード
ord-50962773e1f844a99a633c76cd4c0b37
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…