Trifluoroacetic acid → HCID 56598941, compound

HRID 1522456Notes

Reaction equation

HRID 1522456 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]3[N:10]([CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)[N:11]=[CH:12][C:7]3=[C:6]([C:23]([NH:25][CH2:26][C:27]3[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=3[CH3:33])=[O:24])[CH:5]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:15][CH2:14][CH2:13][N:10]1[C:8]2[N:9]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=[C:6]([C:23]([NH:25][CH2:26][C:27]3[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=3[CH3:33])=[O:24])[C:7]=2[CH:12]=[N:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68078480HCID 68078480, compound

Product 1

HCID 56598941HCID 56598941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {2-[6-cyclopropyl-4-({[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]ethyl}carbamate (260 mg, 0.541 mmol) in DCM (15 mL) was added trifluoroacetic acid (3 ml, 38.9 mmol) and the mixture stirred at room temperature for 2 h. The contents were concentrated in vacuo and the crude residue purified by reverse phase HPLC. (mobile phase: 10 to 70% ACN in H2O, 0.1% NH4OH). The final product was collected as 0.170 g (89%). LCMS E-S (M+H)=353.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (d, J=6.32 Hz, 4 H), 2.13 (s, 3 H), 2.21 (s, 4 H), 3.00 (t, J=6.19 Hz, 2 H), 4.29-4.47 (m, 4 H), 5.90 (s, 1 H,) 7.43 (s, 1 H), 8.22 (s, 1 H), 8.75 (t, 1 H).

Workup

  1. concentrationThe contents were concentrated in vacuo
  2. customthe crude residue purified by reverse phase HPLC
  3. customThe final product was collected as 0.170 g (89%)

Sources & evidence

ORD record
ord-836b35f44b3e4a60be9c619e77235304
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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