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

HRID 1055716ノート

反応式

HRID 1055716 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.[N:23]1([C:29]2[CH:30]=[C:31]([CH:35]=[C:36]([S:38]([F:43])([F:42])([F:41])([F:40])[F:39])[CH:37]=2)[C:32](O)=[O:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[OH-].[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:32](=[O:33])[C:31]2[CH:35]=[C:36]([S:38]([F:43])([F:39])([F:40])([F:41])[F:42])[CH:37]=[C:29]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:30]=2)=[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

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896996563-(Morpholin-4-yl)-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 89699929N-{4-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

50 mg (0.17 mmol) of the compound of Example 6A, 58 mg (0.17 mmol) of the compound of Example 18A and 79 mg (0.21 mmol) of HATU were dissolved in 1.0 ml of DMF, 38 μl (0.35 mmol) of 4-methylmorpholine were added and the mixture was stirred at RT for 16 h. 10 ml of 0.1 M aqueous sodium hydroxide solution were then added, and the mixture was stirred at RT for another 10 min. The precipitate formed was filtered off, washed with water and dried under high vacuum. This crude product was then purified by preparative HPLC (Method 29). The product fractions were concentrated under reduced pressure and the residue was taken up in ethyl acetate and with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. This gave 55 mg (53% of theory) of the title compound.

後処理

  1. stirringthe mixture was stirred at RT for another 10 min
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried under high vacuum
  6. customThis crude product was then purified by preparative HPLC (Method 29)
  7. concentrationThe product fractions were concentrated under reduced pressure
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-785a9c1c47684c6ca296c450852dc9e6
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

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