Water → 1,1-Dicyclohexyl-3-[4-methyl-5-(4-methyl-piperazine-1-sulfonyl)-thiazol-2-yl]-urea

HRID 2384142Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([NH2:17])[S:5][C:6]=1[S:7]([N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)(=[O:9])=[O:8].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.[CH:30]1([NH:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.O>CN(C1C=CN=CC=1)C.ClC(Cl)C.C(Cl)Cl>[CH:37]1([N:36]([CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[C:23]([NH:17][C:4]2[S:5][C:6]([S:7]([N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)(=[O:9])=[O:8])=[C:2]([CH3:1])[N:3]=2)=[O:24])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared in the microwave oven (EmrysOptimizer®). 4-Methyl-5-(4-methyl-piperazine-1-sulfonyl)-thiazol-2-ylamine (0.04 g; 0.141 mmol), CDI (0.023 g; 0.141 mmol) and DMAP were mixed dichloroethane (1.5 ml) in a microwave vessel (2.5 ml). The reaction mixture was heated 600 sec at 120° C., dicyclohexylamine (0.025 g; 0.141 mmol) dissolved in dichloroethane (0.2 ml) was added through the septum and the reaction mixture was heated for additional 600 sec. at 120° C. To the reaction mixture was added water and DCM (25 ml). The water phase was extracted with DCM (3×25 ml), dried with MgSO4 filtered and evaporated in vacuo to afford the title compound, (84 mg) as a yellow oil. Purification by prep. HPLC gave 3 mg (Yield: 4%)

Workup

customPrepared in the microwave oven (EmrysOptimizer®)
additionwas added through the septum
temperaturethe reaction mixture was heated for additional 600 sec
customat 120° C
extractionThe water phase was extracted with DCM (3×25 ml)
dry with materialdried with MgSO4
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-7d3c7f1ee61c4af0b42e7204b330d77f
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263634B2

Reaction notes

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