Pyridine → HCID 10097050, compound

HRID 853667Notes

Reaction equation

HRID 853667 reaction equation
[CH2:1]([N:8]1[C:19]2[C:11](=[C:12]([OH:31])[C:13]3[C:14](=[O:30])[N:15]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:16](=[O:21])[C:17]=3[C:18]=2[OH:20])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[O:20][C:18]1[C:17]2[C:16](=[O:21])[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:14](=[O:30])[C:13]=2[C:12]([OH:31])=[C:11]2[C:19]=1[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]=[N:10]2)[CH3:43]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 178515141HCID 178515141, compound

Product 1

HCID 10097050HCID 10097050, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-6-(4-fluoro-benzyl)-4,8-dihydroxy-1H-1,3,6-triaza-s-indacene-5,7-dione 255 (1 g, 2.39 mmol, 1 equiv.) was dissolved in a flask containing DMF (24 mL, 0.1 M) and pyridine (290 μL, 2.88 mmol, 1.5 equiv.). Ethyl chloroformate was added (231 μL, 2.88 mmol, 1.2 equiv.) under a nitrogen atmosphere. The reaction was stirred for 16 hours before being quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (2×30 mL) and the organic layer washed several times with water (4×30 mL), saturated NaHCO3 (50 mL), brine solution (50 mL). It was dried over Na2SO4, filtered and concentrated in vacuo. Trituration was carried out with Hexanes/Ethyl acetate (1/4, 100 mL) to remove the corresponding biscarbonate to give carbonic acid 3-benzyl-6-(4-fluoro-benzyl)-8-hydroxy-5,7-dioxo-3,5,6,7-tetrahydro-1,3,6-triaza-s-indacen-4-yl ester ethyl ester 256 (13%, 145 mg, 0.296 mmol). 1H NMR (300 MHz) DMSO d6 δ 8.63 (s, 1 H), 7.45-7.35 (m, 6 H), 7.15-7.33 (m, 4 H), 5.59 (s, 2 H), 4.63 (s, 2 H), 3.98 (q, J=6.9 Hz, 2 H), 1.17 (t, J=6.9 Hz, 3 H). MS: 490.2 (M+1). TLC Rf: 0.6 Ethyl acetate.

Workup

  1. custombefore being quenched with saturated NH4Cl (30 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washthe organic layer washed several times with water (4×30 mL), saturated NaHCO3 (50 mL), brine solution (50 mL)
  4. dry with materialIt was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto remove the corresponding biscarbonate

Sources & evidence

ORD record
ord-5c8de6547c9b40fa868fefbc17666ce1
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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