Hydrochloric Acid → N3-[4-[(4-Amino-2-fluorophenyl)methyl]-2-pyridinyl]-N1,N1-dimethyl-1,3-propanediamine

HRID 2374041Notes

Reaction equation

[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13](O)[C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)OC(C)(C)C)=[CH:16][C:15]=2[F:28])[CH:10]=[CH:9][N:8]=1.Cl>CO.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:30])[CH:12]=2)=[C:15]([F:28])[CH:16]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of tert-butyl 4-((2-(3-(dimethylamino)propylamino)pyridine-4-yl)(hydroxy)methyl)-3-fluorophenylcarbamate (80 mg, 0.19 mmol) in MeOH (5.0 mL) was added 2 mL of conc. HCl and palladium on charcoal (10%, 200 mg). The suspension was heated at 75° C. under H2 atmosphere for 24 h. The mixture was cooled down, filtered and concentrated in vacuo. The residue was dissolved in 1 mL of conc. NH4OH and it was extracted with DCM (5×5 mL). The combined organic layer was dried over Na2SO4. After filtration, it was concentrated in vacuo to give 4-(4-amino-2-fluorobenzyl)-N-(3-(dimethylamino)propyl)pyridin-2-amine (31 mg, 40% yield). MS(ESI+): m/z 303.31 (M+H)+.

Workup

temperatureThe mixture was cooled down
filtrationfiltered
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in 1 mL of conc. NH4OH
extractionit was extracted with DCM (5×5 mL)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationAfter filtration, it
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-d52e3133a01e4045a58d01146e9fb21f
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459562B2

Reaction notes

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