Diisopropylethylamine → HCID 90423199, compound

HRID 57514Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH2:13][F:14])[CH2:11][O:10][C:9]2=[O:15])[C:5]([F:16])=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:28][C:27]([C@@H:29]([NH2:31])[CH3:30])=[N:26][CH:25]=2)=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[O:28][C:27]([C@@H:29]([NH:31][C:2]3[N:7]=[C:6]([N:8]4[C@@H:12]([CH2:13][F:14])[CH2:11][O:10][C:9]4=[O:15])[C:5]([F:16])=[CH:4][N:3]=3)[CH3:30])=[N:26][CH:25]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(R)-3-(2,5-difluoropyrimidin-4-yl)-4-(fluoromethyl)oxazolidin-2-one (105 mg, 0.449 mmol), (S)-1-(5-(4-chlorophenyl)oxazol-2-yl)ethanamine (100 mg, 0.449 mmol), and DIPEA (157 ul, 0.898 mmol) were dissolved in DMSO (1 mL) and the reaction mixture was heated at 120° C. for 2 h. The reaction mixture was cooled, diluted with EtOAc, washed with water and brine, and concentrated in vacuo. Column chromatography (5-50% EtOAc/DCM) gave the desired product (169 mg) as a white foam. 1H NMR (400 MHz, CDCl3) b 8.26 (d, J=2.8 Hz, 1H), 7.59-7.50 (m, 2H), 7.45-7.36 (m, 2H), 7.25 (s, 1H), 5.66 (d, J=7.6 Hz, 1H), 5.21 (br s, 1H), 4.86 (ddddd, J=20.0, 8.6, 7.0, 4.3, 2.8 Hz, 1H), 4.66-4.44 (m, 3H), 4.41 (br s, 1H), 1.71 (d, J=7.0 Hz, 3H). HRMS-Acidic. LC-UV/ESI-MS data was recorded on an Acquity LCTp Tof—Rs(FWHM) >12000 Accuracy <5 ppm. Column: Acquity BEHC18 1.7 μm 2.1×50 mm-50° C.

Workup

temperatureThe reaction mixture was cooled
washwashed with water and brine
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d2695cb6cead4e3388d77461c71b01ad
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434719B2

Reaction notes

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