Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(methoxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055755Notes

Reaction equation

HRID 1055755 reaction equation
[CH3:1]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[C:26]1[C:32]([N:33]2[C:40]3[N:36]([N:37]=[C:38]([C:41]4[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=4)[CH:39]=3)[CH:35]=[CH:34]2)=[C:31]([CH3:47])[CH:30]=[CH:29][C:27]=1[NH2:28].[CH3:48][O:49][CH2:50][C:51]1[CH:52]=[C:53]([CH:57]=[C:58]([S:60]([F:65])([F:64])([F:63])([F:62])[F:61])[CH:59]=1)[C:54](O)=[O:55]>CN(C=O)C.CO>[CH3:1][C:29]1[CH:30]=[C:31]([CH3:47])[C:32]([N:33]2[C:40]3[N:36]([N:37]=[C:38]([C:41]4[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=4)[CH:39]=3)[CH:35]=[CH:34]2)=[CH:26][C:27]=1[NH:28][C:54](=[O:55])[C:53]1[CH:57]=[C:58]([S:60]([F:65])([F:64])([F:63])([F:62])[F:61])[CH:59]=[C:51]([CH2:50][O:49][CH3:48])[CH:52]=1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89699939HCID 89699939, compoundHCID 897000823-(Methoxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

Product 1

HCID 89699909N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(methoxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

75 mg (0.198 mmol) of HATU, 24 mg (0.198 mmol) of 4-N,N-dimethylaminopyridine (DMAP) and 50 mg (0.165 mmol) of the compound of Example 11A were added to a solution of 51 mg (0.173 mmol) of the compound of Example 74A in 1 ml of anhydrous DMF. The reaction mixture was stirred at RT for 1 h, then diluted with about 2 ml of methanol and subsequently directly separated into its components by preparative HPLC (Method 32). Evaporation of the product fractions and drying of the residue under high vacuum gave 60 mg (63% of theory) of the title compound.

Workup

  1. customsubsequently directly separated into its components by preparative HPLC (Method 32)
  2. customEvaporation of the product fractions
  3. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-eac742d9687f4defa024ff7f7a338c4f
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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