Itraconazole Impurity 8 → Itraconazole Hydroxy Propyltriazolone Impurity

HRID 527176Notes

Reaction equation

HRID 527176 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:25](=[O:26])[N:24]([CH2:27][CH2:28][CH3:29])[N:23]=[CH:22]4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:25](=[O:26])[N:24]([CH2:27][CH2:28][CH3:29])[N:23]=[CH:22]4)=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 13368248Itraconazole Impurity 8

Product 1

HCID 13368252Itraconazole Hydroxy Propyltriazolone ImpurityYield 97%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

This compound was synthesized as a white amorphous solid from 4c (53.6 mg, 0.136 mmol) in 48% aqueous HBr (1.5 mL) in 97% yield by following general procedure 1.4: 1H NMR (400 MHz, CDCl3, δH) 7.62 (s, 1H), 7.38 (d, J=8.6 Hz, 2H), 7.06-6.90 (m, 4H), 6.74 (d, J=8.4 Hz, 2H), 3.83 (t, J=7.1 Hz, 2H), 3.37-3.31 (m, 4H), 3.24-3.18 (m, 4H), 1.83 (dd, J=14.5, 7.2 Hz, 2H), 0.98 (t, J=7.3 Hz, 3H). MALDI-MS: 380.2 (M+H+), 402.2 (M+Na+).

Sources & evidence

ORD record
ord-a0e12c4b62ae4ca79bffc2e362513f51
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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