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 1055716Notes

Reaction equation

HRID 1055716 reaction equation
[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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-785a9c1c47684c6ca296c450852dc9e6
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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