HCID 86728259, compound → HCID 86728258, compound

HRID 1776856Notes

Reaction equation

HRID 1776856 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]1[N:16]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([F:24])[C:22]=3[CH:23]=[C:15]2[C:14]2[N:25]=[C:26]([C:29]3[C:30]([N:49]([CH3:54])[S:50]([CH3:53])(=[O:52])=[O:51])=[CH:31][C:32]4[O:36][C:35]([C:37]5[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=5)=[C:34]([C:44]([NH:46][CH3:47])=[O:45])[C:33]=4[CH:48]=3)[CH:27]=[CH:28][C:13]=2[O:12]1)C1C=CC=CC=1>CO.[Pd]>[F:24][C:21]1[C:22]2[CH:23]=[C:15]3[C:14]4[N:25]=[C:26]([C:29]5[C:30]([N:49]([CH3:54])[S:50]([CH3:53])(=[O:52])=[O:51])=[CH:31][C:32]6[O:36][C:35]([C:37]7[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=7)=[C:34]([C:44]([NH:46][CH3:47])=[O:45])[C:33]=6[CH:48]=5)[CH:27]=[CH:28][C:13]=4[O:12][CH:11]([CH2:10][CH2:9][OH:8])[N:16]3[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 86728259HCID 86728259, compound

Product 1

HCID 86728258HCID 86728258, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(6-(2-(benzyloxy)ethyl)-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (85 mg, 0.11 mmol) in MeOH (3 mL) was added Pd/C (30 mg, 10%) under H2 protection The mixture was stirred at room temperature overnight. The it was filtered to remove Pd/C, the filtrate was concentrated in vacuo, the resulting residue was purified using prep-TLC (dichloromethane:MeOH=20:1) to provide 5-(11-fluoro-6-(2-hydroxyethyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (60 mg, yield: 85%). And after SFC separation, two enantiomers were obtained. Column: Chiralpak AD-3 50*4.6 mm I.D., 3 um Mobile phase: 60% ethanol (0.05% DEA) in CO2 Flow rate: 3 mL/min Wavelength: 220 nm. Compound 99: RT=0.529 min, Compound 100: RT=1.909 min

Workup

  1. filtrationThe it was filtered
  2. customto remove Pd/C
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-c31833d2cce047a2be334bc039adb792
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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