Trifluoroacetic acid → HCID 86690980, compound

HRID 1055719Notes

Reaction equation

HRID 1055719 reaction equation
CC1C=CC(N)=CC=1N1C2N(N=C(C3C=NC=CC=3)C=2)C=C1.C(OC(NCCOC1C=C(C=C(S(F)(F)(F)(F)F)C=1)C(O)=O)=O)(C)(C)C.[CH3:49][C:50]1[CH:55]=[CH:54][C:53]([NH:56][C:57]([C:59]2[CH:60]=[C:61]([CH:73]=[C:74]([S:76]([F:81])([F:80])([F:79])([F:78])[F:77])[CH:75]=2)[O:62][CH2:63][CH2:64][NH:65]C(=O)OC(C)(C)C)=[O:58])=[CH:52][C:51]=1[N:82]1[C:89]2[N:85]([N:86]=[C:87]([C:90]3[CH:91]=[N:92][CH:93]=[CH:94][CH:95]=3)[CH:88]=2)[CH:84]=[CH:83]1.FC(F)(F)C(O)=O>ClCCl>[NH2:65][CH2:64][CH2:63][O:62][C:61]1[CH:60]=[C:59]([CH:75]=[C:74]([S:76]([F:79])([F:80])([F:81])([F:78])[F:77])[CH:73]=1)[C:57]([NH:56][C:53]1[CH:54]=[CH:55][C:50]([CH3:49])=[C:51]([N:82]2[C:89]3[N:85]([N:86]=[C:87]([C:90]4[CH:91]=[N:92][CH:93]=[CH:94][CH:95]=4)[CH:88]=3)[CH:84]=[CH:83]2)[CH:52]=1)=[O:58]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 86690981HCID 86690981, compoundHCID 89699709HCID 89699709, compoundHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 86690980HCID 86690980, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 mg (0.14 mmol) of the compound of Example 6A and 62 mg (0.15 mmol) of the compound of Example 29A were reacted and worked up analogously to the procedure of Example 16. In this manner, 81 mg (86% of theory) of the Boc-protected intermediate tert-butyl {2-[3-({4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}carbamoyl)-5-(pentafluoro-λ6-sulphanyl)phenoxy]ethyl}carbamate were obtained. This compound was stirred in 1 ml of dichloromethane and 0.5 ml of trifluoroacetic acid at RT for 2 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 61 mg (76% 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-5aaad2573adb4a8ba2000022eb9c99c4
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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