Triethylamine → n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfonamide

HRID 723608Notes

Reaction equation

HRID 723608 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].C(N(CC)CC)C.[O:29]=[C:30]1[NH:35][C:34](=[O:36])[C:33]([S:37](Cl)(=[O:39])=[O:38])=[CH:32][NH:31]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][S:37]([C:33]2[C:34](=[O:36])[NH:35][C:30](=[O:29])[NH:31][CH:32]=2)(=[O:38])=[O:39])[C:10]=1[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2346202,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chlorideHCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

Product 1

HCID 10278640n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the amine of Example 43 (6.5 mg, 20 μmol) and triethylamine (6 μl, 40 μmol) in dimethylformamide (250 μL) was treated with 2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfonyl chloride (J. Am. Chem. Soc., 1956, 78, 401) (0.8 mg, 4.0 μmol) and the mixture was shaken for 18 hours. The reaction mixture was filtered and the filtrate was purified by HPLC (Hypersil Thermoquest Luna C8 150×10 mm column; a gradient mobile phase was used, 10:90 (by volume)→95:5 (by volume) acetonitrile:(water, 95% by volume/trifluoroacetic acid, 0.1% by volume/acetonitrile 5%, by volume)).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by HPLC (Hypersil Thermoquest Luna C8 150×10 mm column

Sources & evidence

ORD record
ord-6892799b018f40609c681171d027aa03
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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