HCID 59231991, compound → HCID 59232077, compound

HRID 1972761Notes

Reaction equation

HRID 1972761 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=3)[N:6]2[N:5]=[CH:4][N:3]=1>C(O)(=O)C.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 59231991HCID 59231991, compound

Product 1

HCID 59232077HCID 59232077, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a dry flask purged with N2 was added platinum(IV) oxide (127 mg, 0.56 mmol) followed by tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate (587 mg, 1.86 mmol) as a solution in acetic acid (19 mL). The mixture was stirred under an H2 atmosphere for 16 h. The mixture was filtered through a pad of Celite® rinsing with acetic acid and ethanol. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The organic was washed with saturated aqueous NaHCO3 (2×75 mL) and the aqueous mixture was back extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness to afford 610 mg (100%) of the desired product as a gray solid. 1H NMR (300 MHz, DMSO-d6) δ 7.78 (s, 1 H), 7.57 (br s, 2 H), 6.78 (d, 1 H), 6.42 (d, 1 H), 4.08-3.97 (m, 2H), 3.28-3.18 (m, 1 H), 1.94 (d, 2 H), 1.55-1.42 (m, 2 H), 1.41 (s, 9 H); ES-MS m/z 318.1 [M+H]+, HPLC RT (min) 2.21.

Workup

  1. customTo a dry flask purged with N2
  2. filtrationThe mixture was filtered through a pad of Celite®
  3. washrinsing with acetic acid and ethanol
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  6. washThe organic was washed with saturated aqueous NaHCO3 (2×75 mL)
  7. extractionthe aqueous mixture was back extracted with ethyl acetate (3×50 mL)
  8. washThe combined organics were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d95019d32f62481980d74a63802cbc24
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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