Ammonium Hydroxide → HCID 21114501, compound

HRID 493726Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH3:18])[C:6]=1[Cl:19].[NH4+:21].[OH-]>>[Cl:19][C:6]1[C:7]([CH3:18])=[CH:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:10][C:5]=1[CH2:4][C:3]([NH2:21])=[O:2]

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 68904647HCID 68904647, compound

Product 1

HCID 21114501HCID 21114501, compound

Procedure

(5-Bromo-2-chloro-3-methyl-phenyl)-acetic acid methyl ester (2.0 g, 7.2 mmol), N-methylpiperazine (960 μL, 8.6 mmol) and Cs2CO3 (3.3 g, 10.1 mmol) are suspended in toluene (80 mL). Pd(OAc)2 (81 mg, 0.36 mmol) and BINAP (224 mg, 0.36 mmol) are added and the reaction is stirred at 100° C. overnight. The mixture is filtered through Celite and the solvent is evaporated. The residue is purified by FCC (AcOEt/AcOH/H2O 60:15:15) to afford 2-[2-chloro-3-methyl-5-(4-methyl-piperazin-1-yl)-phenyl]-acetic acid methyl ester. The ester is suspended in NH4OH 25% (60 mL). The mixture is stirred overnight at RT and the precipitate is filtered off to yield the amide. 1H NMR (DMSO, 400 MHz) δ 2.20 (s, 3H), 2.27 (s, 3H), 2.40-2.45 (m, 4H), 3.07-3.13 (m, 4H), 3.48 (s, 2H), 6.78 (s, 1H), 6.82 (s, 1H), 6.91 (br s, 1H), 7.34 (br s, 1H).

Workup

filtrationthe precipitate is filtered off

Sources & evidence

ORD record: ord-3581157ab3b94c3292cca7da00f9ab35
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534808B2

Reaction notes

Loading…