Cyclobutylamine → HCID 72191222, compound

HRID 531318Notes

Reaction equation

[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[C:27]([CH3:32])=[N:28][O:29][C:30]=4[CH3:31])=[CH:24][N:23]=[C:22](S(C)(=O)=O)[N:21]=3)[C@H:14]2[CH3:37])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:40]1([NH2:44])[CH2:43][CH2:42]C1>C1COCC1>[N:44]1([C:22]2[N:21]=[C:20]([CH2:19][N:15]3[C@@H:14]([CH3:37])[C@@H:13]([C:5]4[CH:4]=[C:3]([C:2]([F:39])([F:38])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=4)[O:17][C:16]3=[O:18])[C:25]([C:26]3[C:27]([CH3:32])=[N:28][O:29][C:30]=3[CH3:31])=[CH:24][N:23]=2)[CH2:40][CH2:43][CH2:42]1

Participants

Conditions

Temperature: 150 °C

Procedure

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(3,5-dimethylisoxazol-4-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one was dissolved in an excess amount of cyclobutylamine in THF, then heated to 150° C. for 2 hours in a microwave reactor. The reaction mixture was evaporated, then reconstituted in methanol and purified by preparative reverse phase HPLC to give the title compound. LCMS (M+H)+: 556.1. 1H NMR (CDCl3, 500 MHz): δ 8.15 (s, 1H), 7.91 (s, 1H), 7.74 (s, 2H), 5.77 (d, 1H), 4.50-4.30 (m, 6H), 3.92 (t, 1H), 2.53 (m, 2H), 2.32 (d, 3H), 2.16 (d, 3H), 0.77 (d, 3H). RTA IC50: 271 nM.

Workup

customThe reaction mixture was evaporated
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-04ee9650ad37483187c86dd115fb41a5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353101B2

Reaction notes

Loading…