Potassium Acetate → HCID 71233350, compound

HRID 2409941Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[CH2:17]2)[CH:3]=1.[C:32]([O-:35])(=[O:34])C.[K+]>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:29][C:28]([F:31])([F:30])[C:25]1[CH:26]=[CH:27][C:22]([N:18]2[CH2:19][CH2:20][CH2:21][C@H:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]3[NH:8][C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=3)[C:32]([OH:35])=[O:34])[CH2:17]2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (1R,2R)—N1-(4-bromopyridin-2-yl)-N2-((S)-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine (40 mg, 0.080 mmol), potassium acetate (31.6 mg, 0.322 mmol), palladium(II) acetate (3.6 mg, 0.016 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (35.7 mg, 0.064 mmol) in DMSO (0.5 mL) was purged with carbon monoxide for 5 min, then stirred under a CO balloon at 60° C. for 14 hr. DMSO was removed by vacuum and the residue was dissolved in acetonitrile, filtered, and the filtrate was concentrated. The residue was purified by RP prep-HPLC (method C) to afford 2-(((1R,2R)-2-(((S)-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)amino)cyclohexyl)amino)isonicotinic acid (32 mg, 0.056 mmol, 69% yield).

Workup

customwas purged with carbon monoxide for 5 min
customDMSO was removed by vacuum
dissolutionthe residue was dissolved in acetonitrile
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by RP prep-HPLC (method C)

Sources & evidence

ORD record: ord-67679a9fb561496eb0e3c920f5069ac4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815909B2

Reaction notes

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