Aniline → [2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yl]-phenyl-amine

HRID 1394193Notes

Reaction equation

Br[C:2]1[C:3]2[N:10]([CH2:11][CH3:12])[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:3]3[C:2]([NH:65][C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)=[CH:7][N:6]=[CH:5][C:4]=3[N:8]=2)=[N:17][O:16][N:15]=1

Participants

Conditions

Temperature: 175 °C

Procedure

Under Ar, a solution of the product from Example 100 (24 mg, 77.6 mol) in 1,4-dioxane (0.8 ml) and toluene (1.2 ml) was treated with Tris(dibenzylidene-acetone)dipalladium (7.2 mg, 7.8 mol), racemic-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (9.7 mg, 15.6 mol), aniline (8.5 l, 93.1 mol), and sodium tert-butoxide (10.5 mg, 108.6 mol). This mixture was then heated to 175° C. by microwave for 45 min. After cooled to ambient temperture, the reaction mixture was diluted with ethyl acetate (30 ml), filtered though a celite pad and then the filtrate was concentrated in vacuo. The residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O), to afford the title compound, (6.3 mg, 24%); MS (ES+) m/e 322 [M+H]+.

Workup

temperatureAfter cooled to ambient temperture
filtrationfiltered though a celite pad
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O)

Sources & evidence

ORD record: ord-10285e050f5646f280c395d8fa8004c8
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348339B2

Reaction notes

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