N,N'-Dimethylethylenediamine → HCID 68570410, compound

HRID 1811555Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26](Br)=[CH:25][C:24]=3[F:30])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:31][S:32]([O-:34])=[O:33].[Na+].CNCCNC>CS(C)=O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([S:32]([CH3:31])(=[O:34])=[O:33])=[CH:25][C:24]=3[F:30])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-[6-(4-bromo-2-fluoro-phenoxy)-5-methoxy-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (0.543 g, 1.21 mmol), sodium methane sulfinate (774.2 mg, 7.58 mmol), and N,N′-dimethyl-ethylene diamine (50.31 μL, 0.44 mmol) and copper (I) trifluoromethane sulfonate benzene complex (384.9 mg, 0.759 mmol) in 20 mL DMSO was heated in microwave for 7 minutes at 120° C. The mixture was purified by HPLC to give compound 4-[6-(2-fluoro-4-methanesulfonyl-phenoxy)-5-methoxy-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (Compound 76) as an oil (242.7 mg, 42%). 1HNMR (DMSO-d6, 400 MHz) δ 1.19-1.21 (d, 6H), 1.68-1.72 (m, 2H), 1.97-2.02 (m, 2H), 3.30-3.33 (m, 2H), 3.33 (s, 3H), 3.65-3.71 (m, 2H), 3.90 (s, 3H), 4.78-4.81 (m, 1H), 5.28-5.37 (m, 1H), 7.69-7.73 (m, 1H), 7.84-7.87 (m, 1H), 8.00-8.03 (m, 1H), 8.16 (s, 1H). Exact mass calculated for C21H26FN3O7S 483.15 found 484.2 (MH+).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-fbb6c5cc8223417fad2c218a26e7a26a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362248B2

Reaction notes

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