HCID 178521762, compound → HCID 178507407, compound

HRID 252834Notes

Reaction equation

HRID 252834 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][N:26]=[N:25][N:24]=2)=[CH:19][CH:18]=1)([O-])=O>[Pd].CO.ClCCl>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[NH:27][N:26]=[N:25][N:24]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 178521762HCID 178521762, compound

Product 1

HCID 178507407HCID 178507407, compoundYield 34.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The nitro compound 171 (20 mg, 0.05 mmol) was hydrogenated (1 atm) in the presence of 10% palladium on charcoal (catalytic amount) in methanol (1 mL) at room temperature for 2-3 hrs. The reaction mixture was filtered through a pad of Celite®, the filtrate was evaporated to give the crude product which was suspended in dichloromethane and stirred overnight at room temperature, then filtered to provide the title compound 172 (6.3 mg, 27% yield). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 9.71 (s, 1H), 8.07 (d, J=8.2 Hz, 2H), 8.00 (d, J=8.2 Hz, 2H), 7.48 (s, 1H), 7.34 (d, J=5.1 Hz, 1H), 7.28 (dd, J=8.2, 2.0 Hz, 1H), 7.24 (d, J=3.5 Hz, 1H), 7.03 (t, J=3.7 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 5.17 (s, 2H). MS: 362.09 (calc), 363.1 (obs).

Workup

  1. customat room temperature
  2. customfor 2-3 hrs
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. customthe filtrate was evaporated
  5. customto give the crude product which
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7042cfe2d4a44c04b5c86b62c97456d6
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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