1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)-N-((R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

HRID 1444723Notes

Reaction equation

HRID 1444723 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@@H:3]1[CH2:18][C:19]([OH:21])=O.[N:22]1([CH2:28][CH2:29][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C@H:36]([NH2:40])[CH2:35][CH2:34][CH2:33]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:9])=[O:10])[C@@H:3]1[CH2:18][C:19]([NH:40][C@H:36]1[C:37]2[C:32](=[CH:31][C:30]([CH2:29][CH2:28][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:39][CH:38]=2)[CH2:33][CH2:34][CH2:35]1)=[O:21]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58646020(R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amineHCID 59167870(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Product 1

HCID 686789922-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)-N-((R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid (310 mg, 1.0 mmol), crude (R)-6-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (310 mg, 1.2 mmol), HOBt (135 mg, 1.0 mmol) and EDCI (191 mg, 1.0 mmol) in 1 mL of DMF was stirred overnight at room temperature. After quenching with sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vacuo. Flash chomatography (SiO2, EtOAc/MeOH=100:15 to 100:20 to EtOAc/2.0M NH3 in MeOH=100:10 to 100:15 to 100:20 ) gave the desired product as a white solid. MS: 551.2 (M+1).

Workup

  1. customAfter quenching with sat. NaHCO3 solution
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-70c3718e202840e3ab8cb749f359385f
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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