N,N'-Dimethylethylenediamine → 2-{4-[(1R,2R)-2-({[4-(cyclopropylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}-5-ethylpyrimidine

HRID 1468841Notes

Reaction equation

Br[C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[CH2:11][C@@H:10]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH:28]1([S:31]([O-:33])=[O:32])[CH2:30][CH2:29]1.[Na+].CNCCNC>CS(C)=O>[CH:28]1([S:31]([C:2]2[CH:27]=[CH:26][C:5]([CH2:6][O:7][CH2:8][C@@H:9]3[CH2:11][C@@H:10]3[CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[N:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][N:19]=4)[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)(=[O:33])=[O:32])[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 120 °C

Procedure

The product of example 54 (step A) (100 mg, 0.2 mmol), sodium cyclopropanesulfinate (36 mg, 0.28 mmol), copper (I) trifluoromethanesulfonate benzene complex (6 mg, 0.012 mmol), and N,N′-dimethylethylenediamine (2 mg, 0.02 mmol) were dissolved in DMSO (1 mL), and the solution was heated at 120° C. The solution was partitioned between water and Et2O. The aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (2/1 EtOAc/hexanes) to provide the title compound. MS (ESI) m/z 456 [M+H]+. GPR119 Human EC50: 1.2 nM

Workup

customThe solution was partitioned between water and Et2O
extractionThe aqueous layer was extracted with Et2O
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified via silica gel column chromatography (2/1 EtOAc/hexanes)

Sources & evidence

ORD record: ord-95f3e728e20540ef9b914e06b1247593
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006228B2

Reaction notes

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