1-Perhydro-2H-pyran-2-yl-3-[3-(3-piperidylpropanoylamino)phenyl]-1H-indazole-5-carboxamide → 3-[3-(3-Piperidylpropanoylamino)Phenyl]-1H-Indazole-5-Carboxamide

HRID 1353850Notes

Reaction equation

HRID 1353850 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=2)[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:35])[CH2:27][CH2:28][CH:29]3[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]3)[CH:20]=2)=[N:8]1>C1(C)C=CC=CC=1>[NH:31]1[CH2:32][CH2:33][CH2:34][CH:29]([CH2:28][CH2:27][C:26]([NH:25][C:21]2[CH:20]=[C:19]([C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[C:12]([C:16]([NH2:18])=[O:17])[CH:11]=4)[NH:7][N:8]=3)[CH:24]=[CH:23][CH:22]=2)=[O:35])[CH2:30]1

Participants

3

Reactant 1

HCID 694257341-Perhydro-2H-pyran-2-yl-3-[3-(3-piperidylpropanoylamino)phenyl]-1H-indazole-5-carboxamide

Product 1

HCID 694208913-[3-(3-Piperidylpropanoylamino)Phenyl]-1H-Indazole-5-CarboxamideYield 7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Perhydro-2H-pyran-2-yl-3-[3-(3-piperidylpropanoylamino)phenyl]-1H-indazole-5-carboxamide was suspended in 20 mL of toluene and HCl gas was bubbled through for 15 min. The reaction mixture became gummy and was stirred at room temperature overnight. The supernatant solution was decanted and the residue was purified by preparatory HPLC. (0.017 g, 7% yield over 2 steps): 1H NMR (DMSO d6) δ 13.48 (s, 1H), 10.38 (s, 1H), 8.62 (s, 1H), 8.1 (s, 1H), 7.94 (dd, 1H), 7.94 (dd, 1H), 7.73 (d, 1H), 7.62 (d, 1H), 7.48 (t, 1H), 7.36 (br s, 1H), 2.65 (m, 2H), 2.5 (m, 2H), 2.4 (br s, 4H), 1.52 (m, 4H), 1.40 (m, 2H); ES-MS (m/z) 392 [M+H]+.

Workup

  1. customHCl gas was bubbled through for 15 min
  2. customThe supernatant solution was decanted
  3. customthe residue was purified by preparatory HPLC

Sources & evidence

ORD record
ord-f0e3df575ab143a680e23a8791d38e46
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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