Triphenylphosphine → 2-[4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-methylphenyl]-N,N-dimethylacetamide

HRID 1474671Notes

Reaction equation

HRID 1474671 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])=[C:23]([CH3:33])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][O:19][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([N:30]([CH3:31])[CH3:32])=[O:29])=[C:23]([CH3:33])[CH:22]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 581286112-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanolHCID 867111812-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide

Product 1

HCID 715731762-[4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-methylphenyl]-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (90 mg, 0.319 mmol) was dissolved in toluene (1 ml) and 2-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide (62 mg, 0.319 mmol), triphenylphosphine (126 mg, 0.479 mmol), and DIAD (93 μl, 0.479 mmol) added and the mixture stirred at RT overnight. The mixture was concentrated in vacuo and the residue purified by chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.1% TFA to afford the title compound. LC/MS (m/z): 457 (M+H)+. GPR119 Human EC50: 1.7 nM.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-6b08915cd7e2467e951db02d319fb4a8
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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