N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine → N1-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine

HRID 1042815Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.[C:14]1([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=3)=[N:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:37][C:34]3[CH:33]=[CH:32][C:31]([NH:30][C:23]4[C:24]5[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:20]([C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)=[N:21][N:22]=4)=[CH:36][CH:35]=3)=[CH:3][CH:4]=[N:5]2)=[N:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In a 20 mL sealed tube was dissolved 8-chloro-3-methoxy-1,5-naphthyridine (70 mg, 360 μmol) in DMF (2.00 mL). To this was added N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine (124 mg, 396 μmol) and the reaction mixture was stirred at 70° C. for 17 h. Upon cooling to RT, the mixture was dissolved in DMF and purified using Gilson reverse phase chromatography. The product fractions were combined, concentrated and the resulting crude was extracted into DCM, washed 1× sodium carbonate, 1×H2O, dried with Na2SO4, filtered through flitted funnel, concentrated to yield N1-(7-methoxy-1,5-naphthyridin-4-yl)-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as light yellow solid. MS [M+H]=471.0; Calc'd 470.5 for C29H22N6O.

Workup

customIn a 20 mL sealed tube
temperatureUpon cooling to RT
custompurified
concentrationconcentrated
extractionthe resulting crude was extracted into DCM
washwashed 1× sodium carbonate, 1×H2O
dry with materialdried with Na2SO4
filtrationfiltered through flitted funnel
concentrationconcentrated

Sources & evidence

ORD record: ord-7b09359350a841dd8bf1efcad70e6d08
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557816B2

Reaction notes

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