Binap, (A+-)- → N-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]thio}phenyl)acetamide

HRID 1986377Notes

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.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.[SH:65][C:66]1[CH:67]=[C:68]([NH:72][C:73](=[O:75])[CH3:74])[CH:69]=[CH:70][CH:71]=1.CC(C)([O-])C.[Na+]>COCCOC.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:4]3[CH:3]=[C:2]([S:65][C:66]4[CH:67]=[C:68]([NH:72][C:73](=[O:75])[CH3:74])[CH:69]=[CH:70][CH:71]=4)[N:7]=[CH:6][C:5]=3[N:8]=2)=[N:17][O:16][N:15]=1

Participants

Conditions

Temperature: 175 °C

Procedure

Under Ar, a suspension of the product from Example 9, Step 2 (50 mg, 162 μmol) in DME (1.4 mL) and toluene (2.8 mL) was treated with tris(dibenzylidene-acetone)dipalladium (15 mg, 16 μmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (20 mg, 32 μmol), N-(3-mercaptophenyl)acetamide (32.6 mg, 195 μmol), and sodium tert-butoxide (22 mg, 227 μmol). This mixture was then heated to 175° C. by microwave for 15 min. After cooling to rt, the reaction mixture was diluted with ethyl acetate (30 ml), filtered through a celite pad and the filtrate was concentrated in vacuo. The residue was purified by reverse phase HPLC to give the title compound (17 mg, 26%). MS (ES+) m/e 396 [M+H]+.

Workup

temperatureAfter cooling to rt
filtrationfiltered through a celite pad
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-bebbe6a0e86647fea77654aa023ae4be
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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