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

HRID 1272947Notes

Reaction equation

HRID 1272947 reaction equation
[CH3:1][N:2]([CH3:31])[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>[CH3:1][N:2]([CH3:31])[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

3

Reactant 1

HCID 224797243-{3-[2-(Dimethylamino)acetylamino]phenyl}-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

Product 1

HCID 224801343-{3-[2-(Dimethylamino)acetylamino]Phenyl}-1H-Indazole-5-CarboxamideYield 13.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-{3-[2-(Dimethylamino)acetylamino]phenyl}-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide was suspended in toluene (10 mL) and HCl gas was bubbled through the suspension for 15 min. The reaction was then stirred at room temperature overnight. After neutralization with aqueous NaHCO3, the reaction mixture was evaporated to dryness and purified by preparatory HPLC. (0.027 g, 13.5% yield over 2 steps): 1H NMR (CD3OD) 8.66 (s, 1H), 8.22 (t, 1H), 7.97 (dd, 1H), 7.75 (t, 2H), 7.63 (d, 2H), 7.51 (t, 1H), 3.21 (s, 2H), 2.41 (s, 6H); ES-MS (m/z) 338 [M+H]+.

Workup

  1. customHCl gas was bubbled through the suspension 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-5674bc8780aa4cbaa681ef6c85f911b3
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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