(2S)-2-Methyloxirane → (2S)-1-{4-[({(1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}methoxy)methyl]phenyl}propan-2-ol

HRID 1468844Notes

Reaction equation

HRID 1468844 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.[CH2:28]1[O:31][C@H:29]1[CH3:30]>>[CH2:24]([C:21]1[CH:20]=[N:19][C:18]([N:15]2[CH2:16][CH2:17][CH:12]([C@H:10]3[CH2:11][C@H:9]3[CH2:8][O:7][CH2:6][C:5]3[CH:26]=[CH:27][C:2]([CH2:28][C@@H:29]([OH:31])[CH3:30])=[CH:3][CH:4]=3)[CH2:13][CH2:14]2)=[N:23][CH:22]=1)[CH3:25]

Participants

3

Reactant 2

HCID 146262(2S)-2-MethyloxiraneHCID 711352722-[4-((1R,2R)-2-{[(4-bromobenzyl)oxy]methyl}cyclopropyl)piperidin-1-yl]-5-ethyl pyrimidine

Product 1

HCID 71136245(2S)-1-{4-[({(1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}methoxy)methyl]phenyl}propan-2-ol

Procedure

This compound was prepared from the product of example 54 (step A), and (S)-propylene oxide according to the procedure from example 58. MS (ESI) m/z 410 [M+H]+. GPR119 Human EC50: 1.6 nM

Sources & evidence

ORD record
ord-761ba5c492a141b6956b9c1e524802bb
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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