Morpholine → 5-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-morpholinobenzofuran-3-carboxamide

HRID 595577Notes

Reaction equation

[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of compound 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.1 mmol) in pyridine (3 mL) was added morpholine (18 mg, 0.2 mol) under N2, and then the mixture was stirred at 60° C. for 3 hours. After concentration in vacuo, DCM was added and the resulting residue was washed with 10% HCl (a.q., 3 mL) and dried over Na2SO4. After concentration, the residue was purified by prep-TLC (DCM:MeOH=20:1) to give the product of 5-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-morpholinobenzofuran-3-carboxamide (20 mg, yield: 44%). 1H-NMR (CDCl3, 400 MHz) δ 8.05 (s, 1H), 7.47 (s, 1H), 6.48 (s, 1H), 3.86 (t, J=4.4 Hz, 4H), 3.46 (t, J=6.4 Hz, 4H), 3.28 (s, 3H), 3.04 (s, 3H), 2.99 (d, J=4.8 Hz, 3H). MS (M+H)+: 446/448.

Workup

concentrationAfter concentration in vacuo, DCM
additionwas added
washthe resulting residue was washed with 10% HCl (a.q., 3 mL)
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe residue was purified by prep-TLC (DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-a12e8398de724f95a167218dab825cdb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242998B2

Reaction notes

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