HCID 69671428, compound → HCID 89809806, compound

HRID 626737Notes

Reaction equation

HRID 626737 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[C:20]3=[CH:21][N:22]([C:24]4[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:31])[N:23]=[C:19]3[C:18]([Br:32])=[CH:17][N:16]=2)[N:11]=[CH:10][N:9]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Br:32][C:18]1[C:19]2[C:20](=[CH:21][N:22]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[N:23]=2)[C:15]([NH:14][C:12]2[CH:13]=[C:8]([NH2:7])[N:9]=[CH:10][N:11]=2)=[N:16][CH:17]=1

Participants

4

Reactant 1

HCID 69671428HCID 69671428, compound

Product 1

HCID 89809806HCID 89809806, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {6-[7-bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]-pyrimidin-4-yl}-carbamic acid tert-butyl ester (95 mg, 0.18 mmol) in DCM (2 mL) and TFA (1 mL) was stirred at room temperature for 3 hours. The solvent was removed and the residue partitioned between DCM and NaHCO3 (sat. aq.). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70-90% ethyl acetate in cyclohexane), to afford the title compound as a white solid (23 mg, 29% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.22 (s, 1H), 9.29 (s, 1H), 8.15 (d, J=0.9 Hz, 1H), 8.04 (s, 1H), 7.84 (d, J=1.2 Hz, 1H), 7.82 (s, 1H), 7.73 (dd, J=7.1 and 9.0 Hz, 1H), 7.59 (d, J=1.2 Hz, 1H), 6.74 (br s, 2H). LCMS (Method B): RT=3.25 min, m/z: 450 [M+H+].

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between DCM and NaHCO3 (sat. aq.)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (70-90% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-9eb832ac0aa745a7997133cd9660af0d
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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