Sodium Bicarbonate → HCID 178479640, compound

HRID 657091Notes

Reaction equation

HRID 657091 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:13][NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=4)[CH:26]=[CH:25][C:24]3=[O:34])[CH2:17][CH2:16]2)[NH:5][C:6]2[C:7]=1[O:8][CH2:9][C:10](=[O:12])[N:11]=2.C([O-])(O)=O.[Na+].[H][H]>CO.[Pd]>[ClH:1].[F:33][C:30]1[CH:31]=[C:32]2[C:27]([CH:26]=[CH:25][C:24](=[O:34])[N:23]2[CH2:22][CH2:21][N:18]2[CH2:19][CH2:20][CH:15]([NH:14][CH2:13][C:4]3[NH:5][C:6]4[C:7]([O:8][CH2:9][C:10](=[O:12])[N:11]=4)=[CH:2][N:3]=3)[CH2:16][CH2:17]2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compoundHCID 178516867HCID 178516867, compound

Product 1

HCID 178479640HCID 178479640, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-2-[({1-[2-(7-fluoro-2-oxo-1(2H)-quinolinyl)ethyl]-4-piperidinyl}amino)methyl]-1H-pyrimido[5,4-b][1,4]oxazin-7(6H)-one (see Example 124(j) for a preparation) (67 mg, 0.13 mmol) in methanol (3 mL) was added NaHCO3 (40 mg) followed by 10% palladium over carbon catalyst (30 mg). The resulting mixture was stirred at room temperature under 1 atm of hydrogen (balloon) for 24 h. The reaction mixture was filtered through a nylon filter and the crude residue was purified by chromatography (silica gel) using a 0-20% MeOH/DCM gradient to provide the free base of the title compound (10 mg, 16%).

Workup

  1. filtrationThe reaction mixture was filtered through a nylon
  2. filtrationfilter
  3. customthe crude residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-628880e85b2443428f2a2b2d28325647
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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