Hydrochloric Acid → 3-[6-(4-Acetyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-chloro-1H-pyridin-2-one

HRID 1793712Notes

Reaction equation

HRID 1793712 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:27])[CH3:26])[CH2:21][CH2:20]3)[CH:16]=[C:15]([CH3:28])[C:13]=2[N:14]=1.O.[ClH:30]>O1CCOCC1>[C:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17]2[CH:16]=[C:15]([CH3:28])[C:13]3[N:14]=[C:10]([C:3]4[C:4](=[O:8])[NH:5][CH:6]=[CH:7][C:2]=4[Cl:30])[NH:11][C:12]=3[CH:18]=2)[CH2:20][CH2:21]1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 220213071-{4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazol-5-yl]-piperazin-1-yl}-ethanone

Product 1

HCID 1356816973-[6-(4-Acetyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-chloro-1H-pyridin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-{4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazol-5-yl]-piperazin-1-yl}-ethanone (5.2 g, 10.6 mmol) in 4 M HCl in dioxane (60 mL) was added water (5 mL). The reaction mixture was stirred at room temperature for 14 h. Concentration of the reaction mixture gave the title compound (4.02 g, 100%) which was used for the next step without purification. LCMS (M+H)+ m/z 486 (t=1.55 min.).

Sources & evidence

ORD record
ord-93c4cc724c774189a107cfeb372b15b6
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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