Benzylamine → 2-(4-Amino-furazan-3-yl)-1-ethyl-N-(phenylmethyl)-1H-imidazo[4,5-c]pyridin-6-amine

HRID 1986375Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)[N:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.OC1C=CC=CC=1C(OC1C=CC=CC=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:4]3[CH:3]=[C:2]([NH:26][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:7]=[CH:6][C:5]=3[N:8]=2)=[N:17][O:16][N:15]=1

Participants

Conditions

Temperature: 170 °C

Procedure

Under Ar, a suspension of the product from Example 9, Step 2 (18.9 mg, 61.1 μmol) in DMF (1 mL) was treated with benzylamine (12 μl, 110 μmol), copper iodide (2.3 mg, 12.2 μmol), phenyl 2-hydroxybenzoate (6.6 mg, 30.6 μmol), and potassium carbonate (16.9 mg, 122.2 μmol). This mixture was then heated to 170° C. by microwave for 40 min. After cooling rt, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC to give the title compound (2.6 mg, 10%). MS (ES+) m/e 336 [M+H]+.

Workup

temperatureAfter cooling rt
washwashed with water and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-eff2f13505c44450af0bfc8af1641919
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

Loading…