[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45]1([N:49]2[CH2:55][CH2:54][CH2:53][N:52]([C:56]([N:58]3[CH2:61][CH:60]([NH2:62])[CH2:59]3)=[O:57])[CH2:51][CH2:50]2)[CH2:48][CH2:47][CH2:46]1>CN(C=O)C.C(Cl)Cl>[CH:45]1([N:49]2[CH2:55][CH2:54][CH2:53][N:52]([C:56]([N:58]3[CH2:59][CH:60]([NH:62][C:6]([C:5]4[CH:4]=[N:3][C:2]([CH3:1])=[CH:10][CH:9]=4)=[O:8])[CH2:61]3)=[O:57])[CH2:51][CH2:50]2)[CH2:48][CH2:47][CH2:46]1To a stirred solution of 6-methylnicotinic acid (5.5 mg, 40 μmol) in 1:1 DCM:DMF (1 ml) was added HOBt (12 mg, 87 μmol) followed by HBTU (30 mg, 80 μmol) at room temperature. After 15 minutes 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-amine (10 mg, 40 μmol) was added and the reaction was stirred for 16 hours. The reaction was concentrated at reduced pressure and purified directly via preparative HPLC to give the title compound (5 mg, 34%).
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