HCID 90425395, compound → HCID 90426427, compound

HRID 1049364Notes

Reaction equation

HRID 1049364 reaction equation
[C:1]([O:5][C:6]([N:8]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[N:24][C:25]([N+:28]([O-])=O)=[CH:26][CH:27]=3)[CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[C:34]([O:33][C:31]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[N:24][C:25]([NH2:28])=[CH:26][CH:27]=3)[CH:18]=[CH:17][N:16]=2)=[CH:11][CH:10]=1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 1

HCID 90425395HCID 90425395, compound

Product 1

HCID 90426427HCID 90426427, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6′-(bis(tert-butoxycarbonyl)amino)-4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridine](0.600 g, 1.178 mmol) in EtOAc (15 mL) and MeOH (5 mL) was treated with 10% Pd/C (50% wet, 0.125 g, 1.178 mmol) and hydrogenated (1 atm) for 16 h. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate concentrated to dryness to afford 6′-(bis(tert-butoxycarbonyl)amino)-4-((6-aminopyridin-3-yl)oxy)-[2,3′-bipyridine](0.55 g, 97%) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 9.06 (d, J=2.5 Hz, 1H), 8.53 (d, J=5.7 Hz, 1H), 8.46 (dd, J=8.5, 2.5 Hz, 1H), 7.84 (d, J=3.0 Hz, 1H), 7.63 (d, J=2.4 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.32 (dd, J=8.9, 3.0 Hz, 1H), 6.79 (dd, J=5.7, 2.4 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.03 (s, 2H), 1.40 (s, 18H); MS (ESI) m/z: 480.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-fec36106774d4979abc11148eb3eea6a
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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