[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=O)[CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][C:48]1[C:49]([CH3:57])=[N:50][N:51]([CH2:54][CH2:55][OH:56])[C:52]=1[CH3:53]>C(Cl)Cl.O>[OH:56][CH2:55][CH2:54][N:51]1[C:52]([CH3:53])=[C:48]([NH:47][C:12]([C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:3]2[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=2)=[O:14])[C:49]([CH3:57])=[N:50]1To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (550 mg, 2.71 mmol) in DCM (15 mL), TBTU (1.303 g, 4.06 mmol) and DIPEA (1.39 mL, 8.12 mmol) was added. After stirring for 40 min at rt, 2-(4-amino-3,5-dimethyl-1H-pyrazol-1-yl)ethanol (420 mg, 2.71 mmol) dissolved in DCM (5 mL) was added to the solution and the resulting mixture was stirred at rt for 1 h. The reaction mixture was diluted with DCM and water, the organic layer was separated and the aq. layer was extracted with DCM (2×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by FC (DCM/MeOH 92:8) yielded the title compound as a white solid. LC-MS conditions A: tR=0.70 min, [M+H]+=341.46.
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