HCID 71469053, compound → HCID 70975810, compound

HRID 535485Notes

Reaction equation

HRID 535485 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:29])=[O:10])=[CH:4][CH:3]=1>CO.CN(C=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:29])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 71469053HCID 71469053, compound

Product 1

HCID 70975810HCID 70975810, compoundYield 51.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 5 (38 mg, 0.089 mmol) and a catalytic amount of 10% Pd/C in MeOH (1 mL) and DMF (0.5 mL) was stirred at room temperature under H2 (1 atm) for 3 hours, filtered through celite, and chromatographed (30-60% EtOAc/DCM) to give 17.8 mg of the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 11.75 (s, 1H), 8.78 (dd, J=2.2, 0.7 Hz, 1H), 8.76 (dd, J=4.8, 1.6 Hz, 1H), 8.40-8.43 (m, 1H), 8.06 (ddd, J=7.9, 2.2, 1.7 Hz, 1H), 7.94-8.02 (m, 2H), 7.67-7.75 (m, 1H), 7.61 (ddd, J=7.9, 4.8, 0.8 Hz, 1H), 7.40 (s, 4H), 3.71 (s, 2H); MS (ESI+) M/Z 391 (M+H)+.

Workup

  1. filtrationfiltered through celite
  2. customchromatographed (30-60% EtOAc/DCM)

Sources & evidence

ORD record
ord-dec20109dfa3480685ac0a5cf4c4d979
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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