Hydrochloric Acid → 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]ethanaminium chloride

HRID 505539Notes

Reaction equation

HRID 505539 reaction equation
Cl.[Cl:2][C:3]1[CH:35]=[CH:34][C:6]2[N:7]([CH2:10][C:11]3[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:13]([C:20]([N:22]([CH3:33])[CH2:23][CH2:24][NH:25]C(=O)OC(C)(C)C)=[O:21])[N:12]=3)[N:8]=[N:9][C:5]=2[C:4]=1[O:36][C:37]1[CH:42]=[C:41]([C:43]#[N:44])[CH:40]=[C:39]([Cl:45])[CH:38]=1>O1CCOCC1>[Cl-:2].[Cl:2][C:3]1[CH:35]=[CH:34][C:6]2[N:7]([CH2:10][C:11]3[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:13]([C:20]([N:22]([CH3:33])[CH2:23][CH2:24][NH3+:25])=[O:21])[N:12]=3)[N:8]=[N:9][C:5]=2[C:4]=1[O:36][C:37]1[CH:42]=[C:41]([C:43]#[N:44])[CH:40]=[C:39]([Cl:45])[CH:38]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86624475tert-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}carbamate

Product 1

HCID 684271992-[[(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]ethanaminium chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid in dioxane (4 M, 5 mL) was added to 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}carbamate (620 mg, 974 mmol) at 0° C. After 2 hours, the reaction mixture was concentrated under reduced pressure and the residue crystallized from ethanol. 1H NMR (DMSO-d6) δ 8.68 (d, J=4.5 Hz, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.97 (d, J=9.1 Hz, 1H), 7.90 (s, 1H), 7.82 (m, 1H), 7.55 (m, 1H), 7.43 (m, 1H), 6.50 (s, 2H), 3.65 (m, 2H), 3.1 (m, 5H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue crystallized from ethanol

Sources & evidence

ORD record
ord-11a38d4e7804481bb451f320544605eb
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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