3-[3-(2-methoxyacetylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide → 3-[3-(2-Methoxyacetylamino)Phenyl]-1H-Indazole-5-Carboxamide

HRID 1272930Notes

Reaction equation

HRID 1272930 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([NH2:24])=[O:23])[CH:20]=3)[N:15](C3CCCCO3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5]>C1(C)C=CC=CC=1.Cl>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([NH2:24])=[O:23])[CH:20]=3)[NH:15][N:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 1

HCID 224801093-[3-(2-methoxyacetylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

Product 1

HCID 224798923-[3-(2-Methoxyacetylamino)Phenyl]-1H-Indazole-5-CarboxamideYield 40.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Procedure

Through a suspension of 3-[3-(2-methoxyacetylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide in toluene (10 mL), HCl gas was bubbled for 20 min. After 6 hours at room temperature, the reaction was complete. The pH of the reaction mixture was neutralized using a saturated aqueous NaHCO3 solution before the solvent was removed under reduced pressure. The title compound was isolated as a white solid after purification by preparative HPLC (30–100% acetonitrile/water) (0.078 g, 40.5% yield): 1H NMR (CD3OD) δ 8.63 (dd, 1H), 8.19 (t, 1H), 7.94 (dd, 1H), 7.74 (td, 2H), 7.60 (dd, 1H), 7.49 (t, 1H), 4.06 (s, 2H), 3.49 (s, 3H); ES-MS (m/z) 325 [M+H]+.

Workup

  1. customwas bubbled for 20 min
  2. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-3aaf37fbb9294e338f5144b374a0d7d2
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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