Hydrochloric Acid → HCID 67981130, compound

HRID 1520068Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][N:26]5[C:31](=[O:32])[CH:30]=[CH:29][C:28]([C:33]6[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=6)=[N:27]5)[CH:23]=4)[N:18](C(OC(C)(C)C)=O)[N:17]=3)[N:13]=[N:12]2)=[CH:7][CH:6]=1)=[O:4].CN(C=O)C.CCO.Cl>[OH-].[Na+]>[O:32]=[C:31]1[N:26]([CH2:25][C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[NH:18][N:17]=[C:16]3[C:14]2[N:13]=[N:12][N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=3)[CH:15]=2)[N:27]=[C:28]([C:33]2[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=2)[CH:29]=[CH:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-butyl 3-{1-[4-(methoxycarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-5-[(6-oxo-3-pyridin-4-ylpyridazin-1(6H)-yl)methyl]-1H-indazole-1-carboxylate (88 mg; 0.10 mmol; 1.0 eq.) was suspended in NaOH (5N solution, 0.50 mL), DMF (6 mL) and EtOH (6 mL). The suspension was heated in MW at 80° C. for 10 min. The reaction mixture was allowed to cool to RT and brought to pH 6 by addition HCl (1N solution). The resulting solution was passed through an SCX-2 column and concentrated to give the title compound as a yellow solid (65 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ 13.41 (brs, 1H), 9.28 (s, 1H), 8.70 (dd, J=1.6, 4.5 Hz, 2H), 8.50 (s, 1H), 8.17 (d, J=9.8 Hz, 1H), 8.04 (d, J=8.7 Hz, 2H), 7.99-7.88 (m, 4H), 7.58 (d, J=9.0 Hz, 2H), 7.55-7.47 (m, 1H), 7.17 (d, J=9.8 Hz, 1H), 5.54 (s, 2H). HPLC (Condition A): Rt 2.34 min (purity 93.1%). MS (ESI+): 491.3, MS (ESI−): 489.4.

Workup

temperatureto cool to RT
concentrationconcentrated

Sources & evidence

ORD record: ord-680b7d86e28d4123a78613183350040f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073892B2

Reaction notes

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