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

HRID 1055712Notes

Reaction equation

HRID 1055712 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.[F:23][S:24]([F:37])([F:36])([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29].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+]>CN(C=O)C>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([S:24]([F:37])([F:23])([F:34])([F:35])[F:36])[CH:26]=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 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27792093-(Pentafluorosulfanyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 89700162N-{4-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.52 mmol) of the compound of Example 6A, 128 mg (0.52 mmol) of 3-(pentafluoro-λ6-sulphanyl)benzoic acid and 237 mg (0.62 mmol) of HATU were initially charged in 1.8 ml of DMF, 0.11 ml (0.62 mmol) of N,N-diisopropylethylamine were added and the reaction was stirred at RT for 1 h. The reaction was then stirred into 15 ml of 0.1 M aqueous sodium hydroxide solution. After a further 10 min of stirring at RT, the precipitate formed was filtered off, washed with water and dried. This gave 235 mg (83% of theory) of the title compound.

Workup

  1. stirringAfter a further 10 min of stirring at RT
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6ec60f5039334d4c81908e508edde83b
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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