1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Cyclohexyl-N-((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

HRID 77417Notes

Reaction equation

HRID 77417 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([N:18]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:46][O:47][C:48]1[CH:75]=[CH:74][C:51]([CH2:52][N:53]([CH2:61][C:62]2[CH:63]=[C:64]3[C:69](=[CH:70][CH:71]=2)[CH2:68][C@@H:67](CN)[CH2:66][CH2:65]3)[CH2:54][CH:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)=[CH:50][CH:49]=1>CN(C=O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:18]([C@H:67]3[CH2:66][CH2:65][C:64]4[C:69](=[CH:70][CH:71]=[C:62]([CH2:61][N:53]([CH2:52][C:51]5[CH:50]=[CH:49][C:48]([O:47][CH3:46])=[CH:75][CH:74]=5)[CH2:54][CH:55]5[CH2:60][CH2:59][O:58][CH2:57][CH2:56]5)[CH:63]=4)[CH2:68]3)[CH3:16])=[O:13])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 883374-Cyclohexylbenzoic acidHCID 66663221((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine

Product 1

HCID 666634144-Cyclohexyl-N-((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-cyclohexylbenzoic acid (45 mg), DMF (1 ml), 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide (hydrochloride, 45 mg) and 1-hydroxybenzotriazole (32 mg) was admixed after 5 minutes with diisopropylethylamine (30 mg) and ((S)-6-{[(4-methoxybenzyl)-(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine (80 mg). Volatile fractions were removed after 12 hours. The residue was purified by preparative HPLC. The product was thus obtained with the molecular weight of 594.84 (C28H38N2O3); MS (ESI) 595 (M+H+).

Workup

  1. customVolatile fractions were removed after 12 hours
  2. customThe residue was purified by preparative HPLC
  3. customThe product was thus obtained with the molecular weight of 594.84 (C28H38N2O3)

Sources & evidence

ORD record
ord-74f7da7f13c648b3827561fbfc97f193
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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