Methanol → HCID 20605630, compound

HRID 481092Notes

Reaction equation

HRID 481092 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:21](=O)[CH:20](Br)[CH2:19][CH2:18][CH2:17][C:7]=2[N:8](C(OC(C)(C)C)=O)[CH:9]=1)=[O:4].Cl.[C:25]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)(=[NH:27])[NH2:26].C([O-])(O)=O.[Na+].CO>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:21]3[N:26]=[C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[NH:27][C:20]=3[CH2:19][CH2:18][CH2:17][C:7]=2[NH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 2776844Pyridine-4-amidine hydrochlorideHCID 20872400HCID 20872400, compound

Product 1

HCID 20605630HCID 20605630, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-Bromo-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester(467 mg, 1.2 mmol), 4-Amidinopyridine hydrochloride(953 mg, 6.1 mmol), and NaHCO3(813 mg, 9.7 mmol) in dioxane(20 mL) is refluxed for 20 h. After cooling to RT, MeOH(5 mL) is added and the mixture is filtered. The filtrate is concentrated in vacuo and the brown residue is purified by flash chromatography on silica gel (10% MeOH/CH2Cl2) to yield 197 mg of 2-Pyridin-4-yl-4,5,6,7-tetrahydro-3H-1,3,7-triaza-cyclopenta[e]azulene-9-carboxylic acid methyl ester as a yellow solid (53%). 1H NMR (CDCl3) 2.06 (quint, 2H), 2.98 (t, 2H), 3.04 (t, 2H), 3.91 (s, 1H), 7.46 (s, 1H), 7.76 (d, 2H) 8.28 (br s, 1H) 8.56 (d, 2H)

Workup

  1. temperatureis refluxed for 20 h
  2. filtrationthe mixture is filtered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe brown residue is purified by flash chromatography on silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0a903add14a84efd9b02d43b0638f3bf
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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