Morpholine → HCID 178442203, compound

HRID 2113506Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:9]=2[CH2:18][CH2:19][NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:5]=[CH:4][N:3]=1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CN1CCCC1=O>[N:35]1([C:2]2[CH:7]=[C:6]([C:8]3[NH:12][N:11]=[C:10]([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[C:9]=3[CH2:18][CH2:19][NH:20][S:21]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:28][CH:29]=3)(=[O:23])=[O:22])[CH:5]=[CH:4][N:3]=2)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of N- {2-[5-(2-Chloro-pyridin-4-yl)-3-thiophen-2-yl-1H-pyrazol-4-yl]-ethyl}-4-pentyl-benzenesulfonamide (10 mg, 19.4 μmol) and morpholine (17 μl, 194 μmol) in 1-methyl-2-pyrrolidinone (500 μL) was stirred at 190° C. in a seal tube for 3 h. The reaction mixture was concentrated to 2 ml. The crude product was purified by Prep-HPLC. Removal of the solvent in vacuo provided the title compound (8.3 mg, 76% yield). MS m/e 566; HPLC retention time 3.35 min (Method A).

Workup

concentrationThe reaction mixture was concentrated to 2 ml
customThe crude product was purified by Prep-HPLC
customRemoval of the solvent in vacuo

Sources & evidence

ORD record: ord-013391ae96bb4282b22e41cb9b5cecc8
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432271B2

Reaction notes

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