Dimethylcarbamoyl Chloride → HCID 22050270, compound

HRID 1867119Notes

Reaction equation

Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:29])=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:12]([Cl:27])[C:11]2=[O:28])[CH:9]=1.[CH3:30][N:31](C)[C:32](Cl)=[O:33].[CH2:36](N(CC)CC)C.[NH4+].[Cl-]>O1CCCC1>[Cl:27][C:12]1[C:11](=[O:28])[N:10]([C:8]2[CH:9]=[C:4]([CH:5]=[CH:6][C:7]=2[F:29])[CH2:3][N:2]([CH3:36])[C:32]([NH:31][CH3:30])=[O:33])[C:15]([CH3:16])=[CH:14][C:13]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26]

Participants

Conditions

Temperature: 25 °C

Procedure

A 10 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with 1-[5-(aminomethyl)-2-fluorophenyl]-3-chloro-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one hydrochloride (250 mg, 0.56 mmol), dimethylcarbamyl chloride (52 μL, 0.56 mmol), triethylamine (195 μL, 1.4 mmol) and tetrahydrofuran (4.0 mL). After stirring at 25° C. for 5 min the reaction was completed by LC-MS. The reaction mixture was poured into a saturated aqueous NH4Cl solution. The aqueous mixture was extracted with ethyl acetate. The organic phase was dried with Na2SO4 and concentrated in vacuo to obtain the desired product (245 mg, 86%) as a white solid. 1H NMR (400 MHz, (CD3OD) δ 7.61 (q, J=7.9 and 6.7 Hz, 1H), 7.4 (m, 1H), 7.3 (d, J=9.3 Hz, 1H), 7.21 (m, 1H), 7.1 (m, 2H), 6.65 (s, 1H), 5.35 (s, 2H), 4.38 (s, 2H), 2.9 (s, 6H), 2.1 (s, 3H) ppm. ES-HRMS m/z 480.1269 (M+H calcd for C23H22ClF3N3O3 requires 480.1296)

Workup

customA 10 mL round bottomed flask equipped with stirbar and nitrogen inlet
extractionThe aqueous mixture was extracted with ethyl acetate
dry with materialThe organic phase was dried with Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2fdb9dabbd7d43d990fe454da145f1e7
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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