Hydrochloric Acid → 1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine hydrochloride

HRID 2064438Notes

Reaction equation

HRID 2064438 reaction equation
[C:1]1([C:7]2[C:8]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:38].CCOC(C)=O>CO.C(Cl)Cl>[ClH:38].[C:1]1([C:7]2[C:8]([C:20]3[CH:21]=[CH:22][C:23]([C:26]4([NH2:30])[CH2:29][CH2:28][CH2:27]4)=[CH:24][CH:25]=3)=[N:9][C:10]3[CH:11]=[CH:12][N:13]4[CH:19]=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57805513HCID 57805513, compound

Product 1

HCID 672540731-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6b) (1.07 g, 2.177 mmol) in MeOH (5 mL) and DCM (15 mL) was added a 4N solution of HCl in EtOAc (5.44 mL, 21.77 mmol). The sealed reaction mixture was permitted to stir at room temperature. After 4 hours the reaction mixture was filtered to give 1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine hydrochloride (1-15) as a tan solid. HRMS (M+H)+: observed=392.1872, calculated=392.1870.

Workup

  1. customThe sealed reaction mixture
  2. filtrationAfter 4 hours the reaction mixture was filtered

Sources & evidence

ORD record
ord-f126e3d6ba724d6ba85487703a40e023
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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