Isopropylamine → (1S,2R)-2-[4'-(2-Hydroxy-1-methyl-4-pyridin-3-yl-butoxy)-biphenyl-4-yl]-N-isopropylactamide

HRID 380027Notes

Reaction equation

HRID 380027 reaction equation
[OH:1][C@H:2]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:3]([CH3:21])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[CH:30]([NH2:33])([CH3:32])[CH3:31].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[OH:1][C@H:2]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:3]([CH3:21])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 757711-HydroxybenzotriazoleHCID 53784232HCID 53784232, compound

Product 1

HCID 59970477(1S,2R)-2-[4'-(2-Hydroxy-1-methyl-4-pyridin-3-yl-butoxy)-biphenyl-4-yl]-N-isopropylactamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S,2R)-[4′-(2-Hydroxy-1-methyl-4-pyridin-3-yl-butoxy)-biphenyl-4-yl]-acetic acid (Example 55, 0.07 g), isopropylamine (0.012 g), 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (0.038 g) and 1-hydroxybenzotriazole (0.027 g) were dissolved in dimethylformamide (2 ml) and stirred for 16 hours at room temperature. The dimethylformamide was removed by vacuum distillation, the residue dissolved in dichloromethane, filtered and purified by normal-phase HPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as a solid (0.061 g).

Workup

  1. customThe dimethylformamide was removed by vacuum distillation
  2. dissolutionthe residue dissolved in dichloromethane
  3. filtrationfiltered
  4. custompurified by normal-phase HPLC
  5. washeluting with a gradient of 0-10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-bc9801c979024f52902090cc0664b69b
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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