Hydrochloric Acid → HCID 67981086, compound

HRID 1520062Notes

Reaction equation

HRID 1520062 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([CH:29]6[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]6)[CH:27]=5)[NH:22][N:21]=4)[N:17]=[N:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[ClH:42]>C1OCCOC1.O>[ClH:42].[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([CH:29]6[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]6)[CH:27]=5)[NH:22][N:21]=4)[N:17]=[N:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67981045HCID 67981045, compound

Product 1

HCID 67981086HCID 67981086, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-(3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)piperidine-1-carboxylate (40 mg; 0.07 mmol; 1.0 eq.) in Dioxane-1,4 (3.0 mL) and water (1.0 mL) was added Hydrogen chloride (1 mL of a 4N solution in dioxane, 4.00 mmol; 56 eq.). The resulting solution was stirred at RT for 12 h. Solvent was removed under reduced pressure, the residue was redissolved in ACN and water and lyophilized to give the title compound as a yellow solid (40 mg, 100%). 1H NMR (300 MHz, DMSO) δ 13.38 (brs, 1H), 9.37 (s, 1H), 8.96 (brs, 1H), 8.76 (brs, 1H), 8.23 (s, 1H), 8.19-8.09 (m, 2H), 7.75-7.53 (m, 3H), 7.34 (dd, J=1.4, 8.7 Hz, 1H), 3.80-3.52 (m, 5H), 3.53-3.21 (m, 3H), 3.04 (d, J=5.3 Hz, 4H), 2.15-1.75 (m, 5H). HPLC (Condition A): Rt 2.44 min (purity 93.2%). MS (ES+): 458.5, MS (ESI−): 456.5.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was redissolved in ACN

Sources & evidence

ORD record
ord-1926a3725bc0478eb86aa8b7a6796a31
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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