Pyrrolidine → HCID 59970489, compound

HRID 380029Notes

Reaction equation

HRID 380029 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.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.Cl.CN(C)CCCN=C=NCC.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]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53784232HCID 53784232, compound

Product 1

HCID 59970489HCID 59970489, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 66. (1S,2R)-[4′-(2-Hydroxy-1-methyl-4-pyridin-3-yl-butoxy)-biphenyl-4-yl]-acetic acid (Example 55, 0.07 g),pyrrolidine (0.014 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 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 was 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 glass (0.068 g).

Workup

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

Sources & evidence

ORD record
ord-33fb05ea3fa24cfb83f9a3c26f2103cd
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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