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

HRID 1444733Notes

Reaction equation

HRID 1444733 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](O)=[O:20].[N:22]1([CH:28]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C@H:36]([NH:40]C(=O)OC(C)(C)C)[CH2:35][CH2:34][CH2:33]3)[CH3:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>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]([CH:28]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:29])=[CH:39][CH:38]=2)[CH2:33][CH2:34][CH2:35]1)=[O:20]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59167870(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acidHCID 86602831tert-butyl(R)-6-(1-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydro-naphthalen-1-ylcarbamate

Product 1

HCID 686816712-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)-N-((R)-6-(1-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-2-(3-Oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid (140 mg) and (1R)-6-(1-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (122 mg, prepared in Example 12) are combined in 2 mL of DMF, then EDCI (112 mg) and HOBT (79 mg) are added and the mix is stirred under nitrogen overnight. Next the mix was quenched with sat. sodium bicarb., extracted with ethyl acetate, washed with brine, washed with water, dried with sodium sulfate, and concentrated. The compound was then purified on the varian using 10 to 90% acetonitrile in water to give the product. MS 551 (ESI, pos. ion).

Workup

  1. customNext the mix was quenched with sat. sodium bicarb
  2. extraction, extracted with ethyl acetate
  3. washwashed with brine
  4. washwashed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe compound was then purified on the
  8. customto give the product

Sources & evidence

ORD record
ord-4255a319bfb743ea83adeef9a0a5206c
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…