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Sodium Bicarbonate → 2-Bromo-3-(3-methyl-2-buten-1-yl)-3,5-dihydro-imidazo[4,5-c]pyridin-4-one

HRID 1663321
Notes
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Reaction equation

HRID 1663321 reaction equation
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[Br:16][C:17]1[N:27]([CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[C:20]2[C:21](=[O:26])[NH:22][CH2:23][CH:24](O)[C:19]=2[N:18]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.O1CCCC1>[Br:16][C:17]1[N:27]([CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[C:20]2[C:21](=[O:26])[NH:22][CH:23]=[CH:24][C:19]=2[N:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×HCID 674358652-Bromo-7-hydroxy-3-(3-methyl-2-buten-1-yl)-3,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-4-one

Product 1

HCID 674357902-Bromo-3-(3-methyl-2-buten-1-yl)-3,5-dihydro-imidazo[4,5-c]pyridin-4-one

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1.55 g Burgess reagent (methoxycarbonylsulphamoyl-triethylammonium-N-betaine) are added to 1.60 g of 2-bromo-7-hydroxy-3-(3-methyl-2-buten-1-yl)-3,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-4-one in 20 ml methylene chloride and 4 ml of tetrahydrofuran. The reaction mixture is stirred for eight hours at 60° C., then another 0.3 equivalents Burgess reagent is added. After a further two hours the cooled reaction mixture is combined with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with methylene chloride/methanol (1:0 to 10:1) as eluant.

Workup

  1. customAfter a further two hours the cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. customevaporated down
  5. customThe flask residue is chromatographed through a silica gel column with methylene chloride/methanol (1:0 to 10:1) as eluant

Sources & evidence

ORD record
ord-a9146d0665b14580887171a121e0d858
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08034941B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes