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Hydrochloric Acid → 3-[1-[(6-amino-2H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloroindazol-4-yl]oxy-5-chlorobenzonitrile;hydrochloride

HRID 505512
Notes
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Reaction equation

HRID 505512 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([CH2:11][N:12]3[C:20]4[C:15](=[C:16]([O:22][C:23]5[CH:24]=[C:25]([CH:28]=[C:29]([Cl:31])[CH:30]=5)[C:26]#[N:27])[C:17]([Cl:21])=[CH:18][CH:19]=4)[CH:14]=[N:13]3)[C:5]2=[CH:4][CH:3]=1.Cl>CO.C(Cl)(Cl)Cl>[Cl-:21].[Cl:21][C:17]1[C:16]([O:22][C:23]2[CH:24]=[C:25]([C:26]#[N:27])[CH:28]=[C:29]([Cl:31])[CH:30]=2)=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([CH2:11][C:10]1[C:5]3[C:6](=[N:7][C:2]([NH3+:1])=[CH:3][CH:4]=3)[NH:8][N:9]=1)[N:13]=[CH:14]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178509921HCID 178509921, compound

Product 1

HCID 1785099223-[1-[(6-amino-2H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloroindazol-4-yl]oxy-5-chlorobenzonitrile;hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile (0.936 g, 2.079 mmol) as a solution in 20% methanol in chloroform (300 mL) was added 1N HCl (2.079 mL, 2.079 mmol), and the resulting mixture was then concentrated under reduced pressure. The resulting white paste was diluted with acetonitrile (100 mL) and the solvent evaporated in vacuo. The dilution-evaporation was repeated twice more for a total of three times. The resulting residue was placed under vacuum overnight to give product. 1H NMR (DMSO-d6): 6.7.91 (s, 1H), 7.81 (s, 3H), 7.68-7.60 (m, 2H), 7.48 (s, 1H), 7.37 (s, 1H), 6.50-6.30 (m, 2H), 6.00-5.86 (m, 2H). HRMS (M+1)=450.06

Workup

  1. concentrationthe resulting mixture was then concentrated under reduced pressure
  2. additionThe resulting white paste was diluted with acetonitrile (100 mL)
  3. customthe solvent evaporated in vacuo
  4. customThe dilution-evaporation
  5. customwas placed under vacuum overnight
  6. customto give product

Sources & evidence

ORD record
ord-d8e444afc0434e4cbd2a45d269e7c9ab
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes