Acetamidine monohydrochloride → HCID 20605622, compound

HRID 497408Notes

Reaction equation

HRID 497408 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13](=O)[CH:12](Br)[CH2:11][CH2:10][C:9]=2[N:8](C(OC(C)(C)C)=O)[CH:7]=1)=[O:5])[CH3:2].Cl.[C:25]([NH2:28])(=[NH:27])[CH3:26]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13]3[N:27]=[C:25]([CH3:26])[NH:28][C:12]=3[CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67170Acetamidine monohydrochlorideHCID 208723925-Bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 20605622HCID 20605622, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-4-oxo-4,5,6,7-tetrahydro-indole 1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester-(1.66 mmol) in 15 mL 1,4-dioxane is added acetamidine hydrochloride (3.32 mmol). After stirring under refluxing for 16 hours the solvent is removed in vacuo. To the residue is added 14 mL CHCl3 and 2 mL MeOH and the mixture is stirred for 10 min. The solid is filtered off. The mother liquid is concentrated and is chromatographed using 10% MeOH in CH2Cl2 as mobile phase to yield 2-methyl-3,4,5,6-tetrahydro-imidazo[4,5-e]indole-8-carboxylic acid ethyl ester as a white solid (30%). 1H NMR (DMSO-d6) 1.30 (t, 3H), 2.28 (s, 3H), 2.70 (t, 2H), 2.79 (t, 2H), 4.22 (q, 2H), 7.20 (s, 1H), 10.58 (s, 1H), 11.43 (s, 1H).

Workup

  1. temperatureunder refluxing for 16 hours the solvent
  2. customis removed in vacuo
  3. additionTo the residue is added 14 mL CHCl3 and 2 mL MeOH
  4. stirringthe mixture is stirred for 10 min
  5. filtrationThe solid is filtered off
  6. concentrationThe mother liquid is concentrated
  7. customis chromatographed

Sources & evidence

ORD record
ord-942314c793f54be894e645a5a7c90cfe
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

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