Ammonium Hydroxide → HCID 21114501, compound

HRID 900143Notes

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

(5Bromo-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 ovemight 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-cfe783514a604a8ba6d8e6bc2a5b4731
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358253B2

Reaction notes

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