Triethylamine → HCID 67043719, compound

HRID 1503459Notes

Reaction equation

FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14]3([CH2:34][NH:33][CH2:32]3)[C:15]2([NH:22][S:23]([CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])(=[O:25])=[O:24])[C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1.Cl[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1.CCN(CC)CC>CO>[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14]3([CH2:34][N:33]([C:36]4[N:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:32]3)[C:15]2([NH:22][S:23]([CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])(=[O:25])=[O:24])[C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 6′-bromo-1′-(2-(trimethylsilyl)ethylsulfonamido)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1′-carboxylate trifluoroacetate (0.2196 g, 0.37 mmol) and 2-chloropyrimidine (0.1080 g, 0.94 mmol) in MeOH (4 mL) was added Et3N (0.5 mL) at room temperature. The mixture was stirred at 80° C. for 18 h and then concentrated under reduced pressure. The residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% MeOH/H2O, 0.1% CF3COOH over 8 min and then 90% MeOH/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford 0.0803 g (39%) of methyl 6′-bromo-1-(pyrimidin-2-yl)-1′-(2-(trimethylsilyl)ethylsulfonamido)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1′-carboxylate. LC-MS tR=1.87 min in 3 min chromatography, m/z 553, 555 (MH+).

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%
customover 8 min
wait90% MeOH/H2O, 0.1% CF3COOH over 2 min

Sources & evidence

ORD record: ord-f02135017dfc4f03a74c03fa08b786f2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212153B2

Reaction notes

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