Potassium Carbonate → methyl 3-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylate

HRID 59745Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:4])=[O:3].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>CN(C=O)C>[O:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][N:5]([C:6]2[CH:10]=[CH:9][S:8][C:7]=2[C:11]([O:13][CH3:14])=[O:12])[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 3-(methylsulfonamido)thiophene-2-carboxylate (prepared in an analogous manner as described in Example 8, Scheme 8, Step 1, 500 mg, 2.125 mmol), 4-(2-chloroethyl)morpholine hydrochloride (435 mg, 2.338 mmol) and potassium carbonate (646 mg, 4.68 mmol) in dry DMF (13 ml) was heated at 80° C. for 5 h and stirred at RT for 3 days. The solvent was evaporated, the residue was diluted with EtOAc and washed with H2O and brine; the organic layer was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography on silica gel (DCM/EtOAc=8/2 to 7/3 and then DCM/MeOH=95/5) to afford methyl 3-(N-(2-morpholinoethyl)-methylsulfonamido)thiophene-2-carboxylate (Int. 50) (655 mg, 1.880 mmol, MS/ESI+ 348.9 [MH]+).

Workup

customprepared in an analogous manner
customThe solvent was evaporated
additionthe residue was diluted with EtOAc
washwashed with H2O and brine
dry with materialthe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe crude was purified by flash chromatography on silica gel (DCM/EtOAc=8/2 to 7/3

Sources & evidence

ORD record: ord-6e8217b4537d4cc2a66651400d30ac80
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440954B2

Reaction notes

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