[NH:1]1[CH2:4][CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:7]=[N:8][N:9]([C:11]2([C:14]3[NH:31][C:17]4=[N:18][C:19]([N:22]5[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28](O)=[O:29])[CH2:23]5)=[CH:20][CH:21]=[C:16]4[N:15]=3)[CH2:13][CH2:12]2)[CH:10]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[N:1]1([C:28]([C@@H:24]2[CH2:25][CH2:26][CH2:27][N:22]([C:19]3[N:18]=[C:17]4[NH:31][C:14]([C:11]5([N:9]6[CH:10]=[C:6]([Cl:5])[CH:7]=[N:8]6)[CH2:12][CH2:13]5)=[N:15][C:16]4=[CH:21][CH:20]=3)[CH2:23]2)=[O:29])[CH2:4][CH2:3][CH2:2]1Azetidine (0.1 mL, 1.42 mmol) was added to a solution of (R)-1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (50 mg, 1.29 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (49 mg, 1.29 mmol) and diisopropylethylamine (0.1 mL, 3.88 mmol) in anhydrous dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 2 h, then was partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (35 mg). MS (ES+APCI) (M+H) 426.1; LCMS retention time: 3.440 min (Method S1).
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