Triethylamine → 1-(6-Bromo-imidazo[1,2-a]pyridin-2-yl)-3-[2-(2-isopropyl-2H-tetrazol-5-yl)-ethyl]-urea

HRID 555993Notes

Reaction equation

C(N(CC)CC)C.C1(O[C:15](=[O:27])[NH:16][C:17]2[N:18]=[C:19]3[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]3[CH:26]=2)C=CC=CC=1.Cl.[CH:29]([N:32]1[N:36]=[N:35][C:34]([CH2:37][CH2:38][NH2:39])=[N:33]1)([CH3:31])[CH3:30]>CN1C(=O)CCC1.O>[Br:25][C:22]1[CH:23]=[CH:24][C:19]2[N:20]([CH:26]=[C:17]([NH:16][C:15]([NH:39][CH2:38][CH2:37][C:34]3[N:35]=[N:36][N:32]([CH:29]([CH3:31])[CH3:30])[N:33]=3)=[O:27])[N:18]=2)[CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylamine (0.15 ml, 1.1 mmol) is added to a stirred mixture of (6-bromo-imidazo[1,2-a]pyridin-2-yl)-carbamic acid phenyl ester (Intermediate B1)(0.30 g, 0.90 mmol) and 2-(2-isopropyl-2H-tetrazol-5-yl)-ethylamine hydrochloride (Intermediate D1)(0.207 g, 1.1 mmol) in NMP (3 ml). The reaction mixture is stirred at 80° C. for 2 hours, cooled and diluted with water (100 ml) resulting in a grey precipitate. The solid is collected by filtration and dried in a vacuum oven to afford the title compound. [MH+ 395.09]

Workup

temperaturecooled
customresulting in a grey precipitate
filtrationThe solid is collected by filtration
customdried in a vacuum oven

Sources & evidence

ORD record: ord-268bf53b7ef243cd874d0e916aca8792
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053574B2

Reaction notes

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