Hydrochloric Acid → 1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine dihydrochloride

HRID 2104115Notes

Reaction equation

HRID 2104115 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:14]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]6)=[CH:22][CH:21]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1.[ClH:44].CCOC(C)=O>CO.C(Cl)Cl>[ClH:44].[ClH:44].[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:14]([C:20]5[CH:21]=[CH:22][C:23]([C:26]6([NH2:30])[CH2:27][CH2:28][CH2:29]6)=[CH:24][CH:25]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57805469tert-butyl (1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)carbamate

Product 1

HCID 248095881-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)carbamate (1-8) (2.52 g, 4.41 mmol) in MeOH (5 mL) and DCM (15 mL) was added a 4N solution of HCl in EtOAc (22 mL, 88 mmol). The sealed reaction mixture was permitted to stir at room temperature. After 4 hours the reaction mixture was concentrated in vacuo to give 1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine dihydrochloride (1-9) as a yellow solid. HRMS (M+H)+: observed=472.2249, calculated=472.2244.

Workup

  1. customThe sealed reaction mixture
  2. concentrationAfter 4 hours the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-35ccef2c31eb453c9ef0c8b9facbde14
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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