[CH3:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.CC([N:20]([C@@H:24]([C:27](NC1C=NC(OC2C=CC(C#N)=C(C(C)C)C=2)=CC=1)=[O:28])[CH2:25]C)[C:21](=O)[O-:22])(C)C.Cl>ClCCl>[CH3:25][C@H:24]1[NH:20][C:21](=[O:22])[N:13]([C:12]2[CH:14]=[CH:15][C:9]([O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:10][CH:11]=2)[C:27]1=[O:28]To 4-[(3-methylphenyl)oxy]aniline (90 mg, 0.45 mmol) in dichloromethane (1 mL) was added with shaking at 35° C. an aliquot of approximately 1/3 of solution 1 slowly via syringe (over ca. 1 min). After 30 min, HCl (ca. 0.8 mL) was added and the heterogeneous mixture was heated at 100° C. for 2 hours with shaking, allowing the dichloromethane to distill off through a glass capillary. After cooling to room temperature the aqueous HCl was pipetted off and the residue dried under vacuum. The residue was purified by silica gel chromatography (Biotage instrument, 10 g column) eluting with 0-100% EtOAc/cHex to give after drying the title compound as a solid (30 mg).
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