Dimethylformamide → N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-[(2-methoxy-ethoxy)methyl]-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055763Notes

Reaction equation

HRID 1055763 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:15]=1)C(O)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[C:47]1[C:53]([N:54]2[C:61]3[N:57]([N:58]=[C:59]([C:62]4[CH:63]=[N:64][CH:65]=[CH:66][CH:67]=4)[CH:60]=3)[CH:56]=[CH:55]2)=[C:52]([CH3:68])[CH:51]=[CH:50][C:48]=1N.[CH3:69][N:70]([CH:72]=[O:73])C>>[CH3:48][C:50]1[CH:51]=[C:52]([CH3:68])[C:53]([N:54]2[C:61]3[N:57]([N:58]=[C:59]([C:62]4[CH:63]=[N:64][CH:65]=[CH:66][CH:67]=4)[CH:60]=3)[CH:56]=[CH:55]2)=[CH:47][C:69]=1[NH:70][C:72](=[O:73])[C:9]1[CH:13]=[C:14]([S:16]([F:21])([F:17])([F:19])([F:18])[F:20])[CH:15]=[C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896996673-[(2-Methoxyethoxy)methyl]-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 89699939HCID 89699939, compound

Product 1

HCID 71667404N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-[(2-methoxy-ethoxy)methyl]-5-(pentafluoro-lambda6-sulphanyl)benzamide

Procedure

58 mg (0.173 mmol) of the compound of Example 98A and 75 mg (0.198 mmol) of HATU were dissolved in 1 ml of DMF, and 24 mg (0.198 mmol) of 4-N,N-dimethylaminopyridine (DMAP) were added slowly. 50 mg (0.165 mmol) of the compound of Example 11A were then added. The reaction mixture was stirred at RT for about 16 h and then separated into its components by preparative HPLC (Method 36). Pooling of the product fractions, evaporation and drying of the residue under high vacuum gave 76 mg (75% of theory) of the title compound.

Workup

  1. customseparated into its components by preparative HPLC (Method 36)
  2. customPooling of the product fractions, evaporation
  3. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-965cf988baa345b2bb41fa2a34eaa54d
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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