3-Thiophenamine, tetrahydro-, 1,1-dioxide → 4-(1,1-Dioxotetrahydrothiophen-3-ylamino)-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348498Notes

Reaction equation

HRID 348498 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3]1.CCN(C(C)C)C(C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[C:29](Cl)=[N:30][C:31]([S:34][CH3:35])=[N:32][CH:33]=2)=[O:27])=[CH:21][CH:20]=1>CO>[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[C:29]([NH:1][CH:2]3[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3]3)=[N:30][C:31]([S:34][CH3:35])=[N:32][CH:33]=2)=[O:27])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 228073-Thiophenamine, tetrahydro-, 1,1-dioxideHCID 81531DiisopropylethylamineHCID 188588054-Chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 867604034-(1,1-Dioxotetrahydrothiophen-3-ylamino)-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amideYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-amino-1,1-dioxotetrahydrothiophene (345 mg, 2.01 mmol) in methanol (5 mL) was added DIPEA (350 μL) followed by 4-chloro-2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (200 mg, 0.67 mmol). The mixture was allowed to stir for 16 h. The resulting mixture was poured into ice-water and the resulting solids were collected by filtration. The solids were washed with ethyl acetate and hexanes and were dried. This afforded 147 mg (0.37 mmol, 55% yield) of the titled product as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.78 (d, 1H), 8.65 (s, 1H), 7.65 (m, 2H), 7.18 (m, 2H), 4.87 (m, 1H), 3.52 (m, 1H), 3.35–3.04 (m, 3H), 2.50, M, 1H), 2.22 (m, 1H); MS (EI) m/z 395.05 (M−H)−.

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. washThe solids were washed with ethyl acetate and hexanes
  3. customwere dried

Sources & evidence

ORD record
ord-9a4e01f6a8ea4770a3f348bda284ba12
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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