Hydrochloric Acid → HCID 86690982, compound

HRID 1055720Notes

Reaction equation

HRID 1055720 reaction equation
CC1C=CC(N)=CC=1N1C2N(N=C(C3C=NC=CC=3)C=2)C=C1.C(OC(NCCCOC1C=C(C=C(S(F)(F)(F)(F)F)C=1)C(O)=O)=O)(C)(C)C.[CH3:50][C:51]1[CH:56]=[CH:55][C:54]([NH:57][C:58]([C:60]2[CH:61]=[C:62]([CH:75]=[C:76]([S:78]([F:83])([F:82])([F:81])([F:80])[F:79])[CH:77]=2)[O:63][CH2:64][CH2:65][CH2:66][NH:67]C(=O)OC(C)(C)C)=[O:59])=[CH:53][C:52]=1[N:84]1[C:91]2[N:87]([N:88]=[C:89]([C:92]3[CH:93]=[N:94][CH:95]=[CH:96][CH:97]=3)[CH:90]=2)[CH:86]=[CH:85]1.Cl>O1CCOCC1.CO>[NH2:67][CH2:66][CH2:65][CH2:64][O:63][C:62]1[CH:61]=[C:60]([CH:77]=[C:76]([S:78]([F:80])([F:83])([F:82])([F:81])[F:79])[CH:75]=1)[C:58]([NH:57][C:54]1[CH:55]=[CH:56][C:51]([CH3:50])=[C:52]([N:84]2[C:91]3[N:87]([N:88]=[C:89]([C:92]4[CH:93]=[N:94][CH:95]=[CH:96][CH:97]=4)[CH:90]=3)[CH:86]=[CH:85]2)[CH:53]=1)=[O:59]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 86690983HCID 86690983, compoundHCID 89699859HCID 89699859, compoundHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 86690982HCID 86690982, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

50 mg (0.17 mmol) of the compound of Example 6A and 73 mg (0.17 mmol) of the compound of Example 30A were reacted and worked up analogously to the procedure of Example 16. In this manner, 118 mg (98% of theory) of the Boc-protected intermediate tert-butyl {3-[3-({4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}carbamoyl)-5-(pentafluoro-λ6-sulphanyl)phenoxy]propyl}carbamate were obtained. This compound was dissolved in 3 ml of 1,4-dioxane and 1 ml of methanol, 0.13 ml (0.52 mmol) of a 4 M solution of hydrogen chloride in 1,4-dioxane was added and the mixture was stirred at 80° C. for 1 h. The mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (Method 18). The product-containing fractions were combined and concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and washed successively with saturated potassium carbonate solution and saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue gave 41 mg (38% of theory) of the title compound.

Workup

  1. customwere obtained
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe residue was purified by preparative HPLC (Method 18)
  4. concentrationconcentrated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed successively with saturated potassium carbonate solution and saturated sodium chloride solution
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customDrying of the residue

Sources & evidence

ORD record
ord-68785bf3725f45c8a9c9d6a6f57e2ff6
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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