1-Propanol → HCID 71542003, compound

HRID 1850217Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one (100 mg, 0.444 mmol), (3-(p-tolyl)-1,2,4-oxadiazol-5-yl)methanamine (84 mg, 0.444 mmol, 1.0 equiv), and TEA (0.186 mL, 1.332 mmol, 3.0 equiv) in butan-1-ol (2 mL) was heated at 100° C. for 90 min. Addition of propan-1-ol (1 ml) and heated at 150° C. for 60 min. The reaction mixture was concentrated in vacuo. Flash column (silica, 24 g) eluting w/0-30% EtOAc/DCM afforded (S)-4-Isopropyl-3-{2-[(3-p-tolyl-[1,2,4]oxadiazol-5-ylmethyl)-amino]-pyrimidin-4-yl}-oxazolidin-2-one (95 mg, white foam) in 54.2% yield. HRMS(B) m/z 394.1753 2.38 Min.

Workup

concentrationThe reaction mixture was concentrated in vacuo
washFlash column (silica, 24 g) eluting w/0-30% EtOAc/DCM

Sources & evidence

ORD record: ord-7362a3f8d9824ffa83a9f32b5f6e9992
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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