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 353084Notes

Reaction equation

HRID 353084 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-b23e63897dd64b7390ea87c08841bfab
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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