Cyclopropylamine → HCID 59970476, compound

HRID 380028Notes

Reaction equation

HRID 380028 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]1([NH2:33])[CH2:32][CH2:31]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH:30]1([NH:33][C:18](=[O:19])[CH2:17][C:14]2[CH:13]=[CH:12][C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C@@H:3]([CH3:21])[C@H:2]([OH:1])[CH2:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[CH:10][CH:9]=3)=[CH:16][CH:15]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53784232HCID 53784232, compound

Product 1

HCID 59970476HCID 59970476, compoundYield 81.8%

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), cyclopropylamine (0.011 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 solid (0.063 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-2c7646974d7344778984188ea9baef2f
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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