Sodium Acetate → HCID 178475374, compound

HRID 2254126Notes

Reaction equation

Br[CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([C:12]([F:15])([F:14])[F:13])[N:5]=[C:4](Cl)[C:3]1=2.[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].Cl.[NH:23]1[C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[CH:39]=[CH:38][C:37]([CH2:40][NH2:41])=[CH:36][CH:35]=2)=[N:26][N:25]=[N:24]1>CS(C)=O>[C:17]([O:20][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([C:12]([F:15])([F:14])[F:13])[N:5]=[C:4]([NH:41][CH2:40][C:37]3[CH:38]=[CH:39][C:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[C:27]4[NH:26][N:25]=[N:24][N:23]=4)=[CH:35][CH:36]=3)[C:3]1=2)(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 40 °C

Procedure

To 25 mL of DMSO was added 4.5 g of 5-bromo-4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazoline and 4.7 g of anhydrous sodium acetate. The reaction mixture was warmed for 2 hours at which time 4.1 g of N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amine hydrochloride was added and the reaction was heated to 40° C. overnight. The crude reaction mixture was purified on silica gel (20% methanol/chloroform) to yield the title product (1.9 g, 24%); 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (m, 1H), 7.63 (m, 2H), 7.53 (m, 2H), 7.24 (m, 2H); 7.03 (m, 2H), 5.64 (m, 1H), 4.52 (m,2H), 2.68 (m, 2H), 2.23 (m, 1H), 1.97 (s, 3H), 1.80 (m, 3H); positive DCI MS m/e 510 (M+H). Anal. calcd for C25H22F3N7O2 : C, 58.94; H, 4.35; N, 19.24. Found: C, 58.31; H, 4.30; N, 19.20.

Workup

additionwas added
customThe crude reaction mixture
customwas purified on silica gel (20% methanol/chloroform)

Sources & evidence

ORD record: ord-d9e8fcb86e304f60803f1b0e47348f4c
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05234936

Reaction notes

Loading…