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

HRID 1055713Notes

Reaction equation

HRID 1055713 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.[CH3:23][C:24]1[N:25]([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])[CH:26]=[CH:27][N:28]=1.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>[CH3:23][C:24]1[N:25]([C:29]2[CH:30]=[C:31]([CH:35]=[C:36]([S:38]([F:42])([F:39])([F:40])([F:43])[F:41])[CH:37]=2)[C:32]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]3[C:16]4[N:12]([N:13]=[C:14]([C:17]5[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=5)[CH:15]=4)[CH:11]=[CH:10]3)[CH:4]=2)=[O:33])[CH:26]=[CH:27][N:28]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89699972HCID 89699972, compoundHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 896999373-(2-Methyl-1H-imidazol-1-yl)-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]-phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.17 mmol) of the compound of Example 6A, 57 mg (0.17 mmol) of the compound of Example 26A and 79 mg (0.207 mmol) of HATU were initially charged in 0.6 ml of DMF, 36 μl (0.207 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 16 h. The reaction was then stirred into 10 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 66 mg (62% 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-145c5bbbb0b54d068758a74b1aa6d99a
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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