HCID 86624471, compound → HCID 68427280, compound

HRID 505532Notes

Reaction equation

HRID 505532 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][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:19]([N:21]([CH3:33])[CH2:22][CH2:23][N:24](C)[C:25](=O)OC(C)(C)C)=[O:20])[N:11]=3)[N:7]=[N:8][C:4]=2[C:3]=1[O:36][C:37]1[CH:42]=[C:41]([C:43]#[N:44])[CH:40]=[C:39]([Cl:45])[CH:38]=1>C(O)(C(F)(F)F)=O>[Cl-:1].[Cl:1][C:2]1[CH:35]=[CH:34][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:19]([N:21]([CH3:33])[CH2:22][CH2:23][NH2+:24][CH3:25])=[O:20])[N:11]=3)[N:7]=[N:8][C:4]=2[C:3]=1[O:36][C:37]1[CH:42]=[C:41]([C:43]#[N:44])[CH:40]=[C:39]([Cl:45])[CH:38]=1

Participants

3

Reactant 1

HCID 86624471HCID 86624471, compound

Product 1

HCID 68427280HCID 68427280, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
-78 °C

Procedure

tert-butyl {2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethyl}methylcarbamate (125 mg, 0.192 mmol) was dissolved in TFA (5 mL). After 20 minutes, the reaction was concentrated and the resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions were concentrated under reduced pressure and the resulting solid was dissolved in MeCN (3 mL), cooled to −78° C. and 1N HCl (5 mL) added. This froze and was lyophilized to yield the title compound. 1H NMR (DMSO-d6) δ 8.68 (dd, J=4.5 Hz, J=1.5 Hz, 1H), 8.57 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 8.11 (s, 1H), 7.96 (m, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.72 (m, 1H), 7.58 (m, 1H), 7.44 (dd, J=4.6 Hz, J=8.0 Hz, 1H), 7.35 (m, 1H), 7.28 (m, 1H), 6.50 (s, 2H), 3.70 (s, 3H), 3.20 (s, 2H), 3.00 (s, 2H), 2.20 (m, 3H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe resulting residue was purified by reverse phase chromatography
  3. washeluting with 30-95% MeCN/H2O+0.1% TFA
  4. concentrationProduct fractions were concentrated under reduced pressure
  5. dissolutionthe resulting solid was dissolved in MeCN (3 mL)
  6. addition1N HCl (5 mL) added

Sources & evidence

ORD record
ord-776368795e77426b834a5febd236fe7b
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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