Hydrochloric Acid → HCID 86699012, compound

HRID 1520074Notes

Reaction equation

HRID 1520074 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:41]=[CH:40][C:18]([C:19]([NH:21][C:22]4[CH:23]=[N:24][N:25]([CH:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)[CH:26]=4)=[O:20])=[CH:17][CH:16]=3)[CH:14]=2)=[N:2]1.[ClH:42]>O1CCOCC1.O>[ClH:42].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:21][C:22]4[CH:23]=[N:24][N:25]([CH:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)[CH:26]=4)=[O:20])=[CH:40][CH:41]=3)[CH:14]=2)=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67981310HCID 67981310, compound

Product 1

HCID 86699012HCID 86699012, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of tert-butyl 4-[4-({4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}amino)-1H-pyrazol-1-yl]piperidine-1-carboxylate (100 mg; 0.18 mmol; 1.0 eq.) in Dioxane (3 mL) was added HCl 4N solution in 1,4-dioxane (450 μl of a 4N solution in dioxane; 1.80 mmol; 10 eq.) and one drop of water. The resulting suspension was stirred at RT O/N. Solvent were removed under reduced pressure and the residue was suspended in ACN and filtered to afford the title compound as a beige solid (64 mg; 72%). 1H NMR (300 MHz, DMSO-d6) δ 13.45 (brs, 1H), 10.75 (s, 1H), 9.46 (s, 1H), 9.19-8.73 (m, 2H), 8.38 (d, J=8.1 Hz, 1H), 8.32-8.18 (m, 4H), 8.15 (s, 1H), 7.71 (s, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.52-7.39 (m, 1H), 7.27 (t, J=7.5 Hz, 1H), 4.64-4.42 (m, 1H), 3.48-3.30 (m, 2H), 3.05 (s, 2H), 2.27-2.05 (m, 4H). HPLC (Condition A): Rt 3.06 min (purity 95.7%). MS (ESI+): 454.4, MS (ESI−): 452.3.

Workup

  1. customSolvent were removed under reduced pressure
  2. filtrationfiltered

Sources & evidence

ORD record
ord-58a1c742a29c46c9b8c62c99c73c7f74
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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