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Pyridine → 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 1776872
Notes
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Reaction equation

HRID 1776872 reaction equation
NCC1N2C3C=CC=C(F)C=3C=C2C2N=C([C:21]3[C:22]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:44])=[O:43])=[CH:23][C:24]4[O:28][C:27]([C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)=[C:26]([C:36]([NH:38][CH3:39])=[O:37])[C:25]=4[CH:40]=3)C=CC=2O1.N1C=CC=CC=1.C(Cl)(=O)C>ClCCl.O>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:27]2[O:28][C:24]3[CH:23]=[C:22]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:43])=[O:44])[CH:21]=[CH:40][C:25]=3[C:26]=2[C:36]([NH:38][CH3:39])=[O:37])=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 867282695-(6-(aminomethyl)-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

Product 1

HCID 694717192-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 99.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(6-(aminomethyl)-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 (50 mg, 0.08 mmol), and pyridine (11 mg, 0.14 mmol) in dichloromethane (1 mL) was stirred at room temperature under N2 protection. Then acetyl chloride (11 mg, 0.14 mmol) was added and the solution was stirred at room temperature for 1.5 hours. Then the mixture was diluted with water (50 mL) and extracted with EtOAc (10 mL*3). The combined organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (dichloromethane:MeOH=10:1) to provide 546-(acetamidomethyl)-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 (30 mg, yield: 56.3%). 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 129: RT=0.449 min, Compound 130: RT=1.264 minutes.

Workup

  1. stirringthe solution was stirred at room temperature for 1.5 hours
  2. extractionextracted with EtOAc (10 mL*3)
  3. washThe combined organic layer was washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-2b75bd44482a4d25ac486edf0a635f57
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265773B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes