HCID 136596916, compound → HCID 136387542, compound

HRID 2170222Notes

Reaction equation

HRID 2170222 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[NH:15][C:16]([CH3:24])=[C:17]2[C:22]=1[CH:21]=[N:20][NH:19][C:18]2=[O:23].[H][H]>[Pd].C(OCC)(=O)C>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=2[F:1])=[C:6]([C:14]2[NH:15][C:16]([CH3:24])=[C:17]3[C:22]=2[CH:21]=[N:20][NH:19][C:18]3=[O:23])[CH:7]=1

Participants

5

Reactant 2

HCID 136596916HCID 136596916, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136387542HCID 136387542, compoundYield 73,302.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 78b (80 mg, 0.20 mmol) and 10% palladium on carbon (42.7 mg, 0.040 mmol) in ethyl acetate (20 mL) was treated with a balloon of hydrogen gas. The reaction mixture was stirred at ambient temperature for 16 hours. The solid was removed by filtration, and the filtrate was concentrated. The residue was purified by flash chromatography (silica gel, 2-6% methanol in dichloromethane) to afford the title compound (54 g, 73%). 1 H NMR (300 MHz, DMSO-d6) δ 12.35 (s, 1 H) 11.34 (s, 1 H) 8.00 (s, 1 H) 7.20-7.37 (m, 1 H) 6.85-6.97 (m, 1 H) 6.71-6.83 (m, 3 H) 6.59 (dd, J=8.73, 2.78 Hz, 1 H) 5.18 (s, 2 H) 2.56 (s, 3 H). MS (ESI+) m/z 369 (M+H)+.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (silica gel, 2-6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-17324ac97df946139f89b46177ca6321
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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