Methanol → HCID 69217724, compound

HRID 272759Notes

Reaction equation

HRID 272759 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=2[N+:24]([O-])=O)[CH:3]=1.CO.[H][H]>[Pt].C(OCC)(=O)C>[NH2:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[NH:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 69218763HCID 69218763, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69217724HCID 69217724, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 695B (0.73 g, 1.93 mmol), 5% Pt/C, methanol (15 mL) and ethyl acetate (15 mL) was equipped with a balloon of hydrogen gas and stirred at room temperature. After uptake of the hydrogen was complete, the solution was filtered through diatomaceous earth (Celite®). The filtrate was concentrated under vacuum and the residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 0.64 g (95%) of the desired product. MS (DCI) m/e 349 (M+H)+, 366 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 8.81 (s, 1H), 7.85 (d, J=8.5 Hz, 1H), 6.96 (d, J=8.1 Hz, 1H), 6.69-6.72 (m, 2H), 6.50 (dd, J=7.8, 1.8 Hz, 1H), 6.40 (d, J=2.1 Hz, 1H), 5.00 (s, 2H), 3.86 (s, 3H), 3.63 (s, 3H), 3.55 (s, 2H).

Workup

  1. filtrationthe solution was filtered through diatomaceous earth (Celite®)
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-038058fe4f3646c29b9e571b860fc89a
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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