HCID 67262173, compound → HCID 67256554, compound

HRID 1509199Notes

Reaction equation

HRID 1509199 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:24]=[C:23]([N:25]([CH3:31])[CH2:26][C:27]([O:29]C)=O)[C:22]([N+:32]([O-])=O)=[CH:21][C:20]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:20]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:21][C:22]4[NH:32][C:27](=[O:29])[CH2:26][N:25]([CH3:31])[C:23]=4[N:24]=3)=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 67262173HCID 67262173, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67256554HCID 67256554, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a glass autoclave were added methyl 2-((6-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-3-nitro-5-phenylpyridin-2-yl)(methyl)amino)acetate (800 mg, 1.46 mmol) and 10% palladium on carbon (300 mg, 0.28 mmol) in THF (100 ml). The solution was hydrogenated at room temperature under 1.5 atm hydrogen for 20 hours. The reaction mixture was filtered through celite, then concentrated to dryness under reduced pressure. The residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100) to afford the title compound (270 mg, 38%). 1H NMR (500 MHz, CDCl3): 7.35 (2H, d), 7.20-7.33 (5H, m), 7.15 (2H, d), 6.98 (1H, s), 5.05 (1H, br s), 4.11 (2H, s), 3.18 (3H, s), 2.20-2.70 (4H, br m), 2.00-2.14 (1H, m), 1.77-1.87 (1H, m), 1.10-1.50 (9H, br).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100)

Sources & evidence

ORD record
ord-9dd886e034d54a6bb91270d06c182ec3
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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