tert-butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate → HCID 178509925, compound

HRID 505552Notes

Reaction equation

HRID 505552 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:9][C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[N:12](C(OC(C)(C)C)=O)[N:11]=3)[N:7]=[N:8][C:4]=2[C:3]=1[O:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([C:36]#[N:37])[C:30]=1[Cl:38]>C(O)(C(F)(F)F)=O>[Cl:38][C:30]1[C:29]([O:28][C:3]2[C:4]3[N:8]=[N:7][N:6]([CH2:9][C:10]4[C:18]5[C:13](=[N:14][CH:15]=[CH:16][CH:17]=5)[NH:12][N:11]=4)[C:5]=3[CH:26]=[CH:27][C:2]=2[Cl:1])=[CH:34][C:33]([Cl:35])=[CH:32][C:31]=1[C:36]#[N:37]

Participants

3

Reactant 1

HCID 68428123tert-butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 178509925HCID 178509925, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (569 mg, 0.997 mmol) was dissolved in TFA (5 mL). After 20 minutes, the reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions concentrated under reduced pressure to yield the title compound. 1H NMR (DMSO-d6) δ 8.53 (dd, J=4.4 Hz, J=1.6 Hz, 1H), 8.14 (dd, J=8.0 Hz, J=1.5 Hz, 1H), 8.04 (d, J=0.6 Hz, 1H), 7.89 (d, J=8.9 Hz, 1H), 7.79 (d, J=8.9 Hz, 1H), 7.44 (d, J=0.6 Hz, 1H), 7.21 (dd, J=8.0 Hz, J=4.5 Hz, 1H), 6.38 (d, 2H). HRMS (M+1)=470.0076

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by reverse phase chromatography
  3. washeluting with 30-95% MeCN/H2O+0.1% TFA
  4. concentrationProduct fractions concentrated under reduced pressure

Sources & evidence

ORD record
ord-d7d95ea8aad9476aad0cdc83ca4efebe
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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