HCID 91030395, compound → HCID 59627857, compound

HRID 1256667Notes

Reaction equation

HRID 1256667 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]=[CH:20][C:19]=2[N+:30]([O-])=O)=[O:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:21]=[CH:20][C:19]=2[NH2:30])=[O:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 91030395HCID 91030395, compound

Product 1

HCID 59627857HCID 59627857, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl(4-{[(3-nitro-6-phenylpyridin-4-yl)amino]carbonyl}benzyl)carbamate (30 mg, 0.067 mmoll) in MeOH (2 mL) was added Pd on carbon (˜10 mg) and the reaction flask was thoroughly flushed with H2. The reaction was then allowed to proceed at RT under a H2 balloon. During the course of reaction, the mixture becomes a homogenous solution. The reaction mixture was filtered through a silica gel pad and the silica gel was washed thoroughly with MeOH. The Me0H layer was concentrated and residue was purified by HPLC. 1H NMR (600 MHz. d6-DMSO) δ 9.78 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.91 (d, J=7.8 Hz, 2H), 7.87 (dd, J=8.4, 1.2 Hz, 2H), 7.48 (t, J=6 Hz, 1H), 7.37 (m, 4H), 7.27 (m, 1H), 5.32 (bs, 2H), 4.17 (d, J=6 Hz, 2H), 1.37 (s, 9H); MS: cal'd 419 (M+H)+, exp 419 (M+H)+.

Workup

  1. customthe reaction flask was thoroughly flushed with H2
  2. customto proceed at RT under a H2
  3. customDuring the course of reaction
  4. filtrationThe reaction mixture was filtered through a silica gel pad
  5. washthe silica gel was washed thoroughly with MeOH
  6. concentrationThe Me0H layer was concentrated
  7. customresidue was purified by HPLC

Sources & evidence

ORD record
ord-d6998df8ec0d4a6084252537cecab439
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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