HCID 58967008, compound → HCID 66622250, compound

HRID 416254Notes

Reaction equation

HRID 416254 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([N+:13]([O-])=O)=[C:10]([NH2:12])[CH:11]=1>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[CH:8][C:7]=1[F:16]

Participants

4

Reactant 1

HCID 58967008HCID 58967008, compound

Product 1

HCID 66622250HCID 66622250, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of intermediate 180 (220 mg, 0.904 mmol) in acetic acid (3.6 mL) was degassed and put under N2 atmosphere. A catalytic amount of Pd(OH)2 was added and the black mixture was hydrogenated (1 atm) at rt for 16 h, filtered through a celite pad and rinsed with MeOH. The filtrate was concentrated in vacuo at 80° C. to afford the title compound 181 as a mixture with AcONHEt3 (252 mg, 75%). 1H NMR: (CD3OD) δ (ppm): 6.54 (d, J=7.8 Hz, 1H), 6.51 (d, J=12.3 Hz, 1H), 4.21 (t, J=5.1 Hz, 2H), 3.40 (t, J=5.1 Hz, 2H), 2.89 (s, 6H). m/z: 214.1 (MH+).

Workup

  1. customat rt
  2. customfor 16 h
  3. filtrationfiltered through a celite pad
  4. washrinsed with MeOH
  5. concentrationThe filtrate was concentrated in vacuo at 80° C.

Sources & evidence

ORD record
ord-6ecd1b326d944fee9788d49b541e1a3b
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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