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

HRID 1272937Notes

Reaction equation

HRID 1272937 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([NH2:26])=[O:25])[CH:22]=3)[N:17](C3CCCCO3)[N:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7]>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([NH2:26])=[O:25])[CH:22]=3)[NH:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

3

Reactant 1

HCID 224802233-[3-(2-Furylcarbonylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

Product 1

HCID 224798333-[3-(2-Furylcarbonylamino)Phenyl]-1H-Indazole-5-CarboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-[3-(2-Furylcarbonylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide was suspended in 10 mL of toluene and HCl gas was bubbled through for 15 min. The reaction mixture was stirred at room temperature overnight. After neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness and purified by preparatory HPLC. (0.111 g, 54% yield): 1H NMR (DMSO d6) δ 13.5 (br s, 1H), 10.3 (s, 1H), 8.64 (s, 1H), 8.4 (s, 1H), 8.11 (br s, 1H), 7.97 (s, 1H), 7.92 (t, 2H), 7.8 (d, 1H), 7.6 (d, 1H), 7.52 (t, 1H), 7.39 (d, 1H), 7.36 (s, 1H), 6.7 (t, 1H); ES-MS (m/z) 347 [M+H]+.

Workup

  1. customHCl gas was bubbled through for 15 min
  2. customAfter neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness
  3. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-9bb28f804f614018956ed2e5fd83d9b2
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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