Dimethylamine → HCID 178442201, compound

HRID 2113505Notes

Reaction equation

Br[C:2]1[N: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][CH:3]=1.[CH3:35][NH:36][CH3:37]>CN1CCCC1=O>[CH3:35][N:36]([CH3:37])[C:2]1[N: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][CH:3]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of N-{2-[5-(6-Bromo-pyridin-2-yl)-3-thiophen-2-yl-1H-pyrazol-4-yl]-ethyl}-4-pentyl-benzenesulfonamide (5 mg, 8.9 μmol) and dimethylamine (2.0M in MeOH, 8.0 ml) 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 (1.2 mg, 26% yield). MS m/e 524; HPLC retention time 3.34 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-81d66803ae8146dbbe9b9d706bde4b97
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432271B2

Reaction notes

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