Diisopropylethylamine → (S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-ylcarbamate

HRID 407931Notes

Reaction equation

Cl.[O:2]=[C:3]1[C@@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][CH2:5][N:4]1[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl[C:27]1[N:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][N:28]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:33]([C:30]1[CH:29]=[N:28][C:27]([N:23]2[CH2:24][CH2:25][CH:20]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:3]3=[O:2])[CH2:21][CH2:22]2)=[N:32][CH:31]=1)[CH3:34]

Participants

Conditions

Temperature: 100 °C

Procedure

A flask was charged with (S)-benzyl 2-oxo-1,4′-bipiperidin-3-ylcarbamate hydrochloride (4.1 g, 11 mmol), 2-chloro-5-ethylpyrimidine (1.7 g, 12 mmol), DIEA (3.9 mL, 22 mmol), and DMF (30 mL). The reaction was heated to 100° C. overnight. The reaction was cooled to ambient temperature, concentrated and purified over silica gel (25-75% EtOAc in hexanes) to afford (S)-benzyl 1′-(5-ethylpyrimidin-2-yl)-2-oxo-1,4′-bipiperidin-3-ylcarbamate (2.8 g, 57% yield).

Workup

temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated
custompurified over silica gel (25-75% EtOAc in hexanes)

Sources & evidence

ORD record: ord-f27e27d72cbd461e8a1f28d3c9211e0f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

Loading…