Trifluoroacetic acid → HCID 86689036, compound

HRID 920208Notes

Reaction equation

HRID 920208 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11]C(=O)OC(C)(C)C)[N:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][CH3:26])[CH:20]=2)[N:3]=1.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C:19]3[CH:20]=[C:21]([N:25]([CH3:26])[C:27](=[O:30])[CH:28]=[CH2:29])[CH:22]=[CH:23][CH:24]=3)[N:3]=[C:2]([I:1])[C:10]=12

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13140Acryloyl chlorideHCID 71256053HCID 71256053, compound

Product 1

HCID 86689036HCID 86689036, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-iodo-1-(3-(methylamino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylcarbamate (46) (440 mg, 0.99 mmol) in DCM (8 mL) at 0° C. was added acryloyl chloride (103 mg, 1.13 mmol) dropwise. The resulting mixture was stirred at RT overnight before introducing TFA (8 mL). Stirring was continued for an additional 2 h. Solvents were removed and the residue was dissolved in sat. aquous NaHCO3. The product was extracted with 85% DCM/IPA (50 mL×3). The combined organic extracts were dried over Na2SO4, filtered and concentrated to provide N-(3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-N-methylacrylamide (50) (375 mg, 95%) as a white solid. LC-MS (ESI): m/z (M+1) 421.0.

Workup

  1. stirringStirring
  2. waitwas continued for an additional 2 h
  3. customSolvents were removed
  4. dissolutionthe residue was dissolved in sat. aquous NaHCO3
  5. extractionThe product was extracted with 85% DCM/IPA (50 mL×3)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5cb77bf67dc34150bb7f68a1589ce729
Source dataset
uspto-grants-2016_03
Patent number
US09273051B2

Reaction notes

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