Dichloromethane → HCID 10382943, compound

HRID 736371Notes

Reaction equation

HRID 736371 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:24]([N+:25]([O-])=O)=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl>CCO.[Pd]>[NH2:25][C:24]1[C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=3)=[O:28])=[CH:18][CH:17]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 11749185HCID 11749185, compound

Product 1

HCID 10382943HCID 10382943, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 2 (720 mg, 2.18 mmol) was hydrogenated (balloon apparatus) as a solution in 30 mL of 1:1 EtOH:CH2Cl2 over 10% Pd/C overnight at room temperature. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.22 (s, 1H), 8.04-8.08 (m, 2H), 7.95 (dd, J=4.4 Hz, 1.7 Hz, 1H), 7.70-7.84 (m, 2H), 7.36-7.40 (m, 2H), 7.19 (dd, J=8.2 Hz, 1.7 Hz, 1H), 7.11 (dd, J=8.1 Hz, 4.4 Hz, 1H), 1.29 (s, 9H); MS (ESI+) m/z 346 (M+H)+.

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cacd67e52a154bf8ab43c3dc0d90660b
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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