HCID 58902364, compound → HCID 68062122, compound

HRID 1640199Notes

Reaction equation

HRID 1640199 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH:19]([C:23]([NH:25][C:26]5[CH:27]=[C:28]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=5)[CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:24])[CH2:20]4)=[CH:15][CH:14]=3)[C:5]=2[CH:4]=[CH:3]1>CC(O)=O.[Pt](=O)=O>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH:19]([C:23]([NH:25][C:26]5[CH:27]=[C:28]([CH:38]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:40]=5)[CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:24])[CH2:20]4)=[CH:15][CH:14]=3)[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 58902364HCID 58902364, compound

Product 1

HCID 68062122HCID 68062122, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Platinum dioxide (1.9 mg, 0.0082 mmol) was added to a solution of tert-butyl [3-[({7-[(7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}-carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate (20 mg, 0.033 mmol) in AcOH (0.5 mL). The solution was allowed to stir under an atmosphere of hydrogen at rt. After 28 hr, an additional amount of platinum dioxide was added (1.9 mg, 0.0082 mmol) and the reaction continued to stir under an atmosphere of hydrogen for a total of 46 h. The reaction mixture was then filtered through Celite and the residue was purified by column chromatography to give tert-butyl [3-[({7-[(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4tetrahydronaphthalen-2-yl}carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate (9.0 mg, 45%) as a white solid. LCMS: (FA) ES+ 611.4.

Workup

  1. stirringto stir under an atmosphere of hydrogen for a total of 46 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3c97a642477d4710a891d4df89bbf07c
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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