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Hydrochloric Acid → 4-Iodo-3-(4-methyl-6-piperazin-1-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one

HRID 1793725
Notes
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Reaction equation

HRID 1793725 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:31]=[C:30]([CH3:32])[C:17]3[N:18]=[C:19]([C:21]4[C:22]([O:28]C)=[N:23][CH:24]=[CH:25][C:26]=4[I:27])[NH:20][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[I:27][C:26]1[CH:25]=[CH:24][NH:23][C:22](=[O:28])[C:21]=1[C:19]1[NH:20][C:16]2[CH:15]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:31]=[C:30]([CH3:32])[C:17]=2[N:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 235419074-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1356819084-Iodo-3-(4-methyl-6-piperazin-1-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester (24 g, 43.7 mmol) was added 1,4-dioxane (750 mL) and 6 N aqueous HCl (30 mL) and the mixture was heated to 75° C. overnight. The solution was cooled to room temperature, the supernatent was poured off, and the resulting dark gummy solid was washed with anhydrous diethyl ether (3×500 mL) and dried in vacuo to give 17.7 g (93%) of the title compound as a dark solid that was used as described to prepare 4-[2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester and 4-[2-(4-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester; LCMS (M+H)+ m/z 436. (Note: A small peak (4-chloro-pyridin-2-one) in the LC/MS shows m/z 344, 346).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additionthe supernatent was poured off
  3. washthe resulting dark gummy solid was washed with anhydrous diethyl ether (3×500 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ff01f46f643c444d89ba3edcdaef3be8
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07081454B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes