Tetrahydrofuran → N-(5-Amino-2-(morpholine-4-carbonyl)phenyl)-N-methylmethanesulfonamide

HRID 2044101Notes

Reaction equation

HRID 2044101 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[S:3]([CH3:6])(=[O:5])=[O:4].[Cl-].[NH4+].C1COCC1>CO.[Zn]>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:16]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[O:17])=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:12]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 66833063N-Methyl-N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

Product 1

HCID 57489649N-(5-Amino-2-(morpholine-4-carbonyl)phenyl)-N-methylmethanesulfonamideYield 74%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-methyl-N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide (101.3 mg, 0.295 mmol), zinc (193 mg, 2.95 mmol), ammonium chloride (158 mg, 2.95 mmol) in MeOH (0.5 mL), and THF (0.5 mL) was stirred at room temperature for 16 h. The crude material was loaded onto a silica gel cartridge and dried in vacuo. The dry cartridge was then connected to an ISCO cartridge, eluting with 2-10% MeOH in CH2Cl2 to give the desired product as white solid (68.2 mg, 74% yield). LCMS: (M+H)+=314.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.94 (1H, d, J=8.28 Hz), 6.61 (1H, br. s.), 6.53 (1H, dd, J=8.28, 2.01 Hz), 5.52 (2H, s), 3.51 (4H, br. s.), 3.19-3.26 (1H, m), 3.15-3.18 (3H, m), 3.08 (3H, br. s.), 3.03 (3H, br. s.).

Workup

  1. customdried in vacuo
  2. washeluting with 2-10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-eaf69d98a0824d308add69b495791541
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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