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

HRID 1444716Notes

Reaction equation

HRID 1444716 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.[NH2:22][C@@H:23]1[CH2:32][CH2:31][CH2:30][C:29]2[CH:28]=[C:27]([CH2:33]O)[CH:26]=[CH:25][C:24]1=2.C1C=C[C:38]2N(O)N=[N:41][C:39]=2[CH:40]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH:39]1([NH:41][CH2:33][C:27]2[CH:28]=[C:29]3[C:24](=[CH:25][CH:26]=2)[C@H:23]([NH:22][C:19](=[O:21])[CH2:18][C@@H:3]2[C:2](=[O:1])[NH:7][CH:6]=[CH:5][N:4]2[S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:32][CH2:31][CH2:30]3)[CH2:40][CH2:38]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 16108956[(5R)-5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl]methanolHCID 59167870(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Product 1

HCID 57400696N-((R)-6-((cyclopropylamino)methyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-((R)-3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid (6 g, 19.33 mmol) was dissolved in anhydrous DMF (100 mL). (R)-(5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl)methanol (3.77 g, 21.27 mmol) and HOBt (Aldrich, 3.14 g, 23.20 mmol) were added followed by EDCI (Aldrich, 4.45 g, 23.20 mmol). The mixture was stirred at RT for 5 h. EtOAc (250 mL) was added and the solution was washed with saturated sodium bicarbonate/brine (2×200 mL), then with 10% HCl/brine (200 mL), then with brine (200 mL). It was concentrated and dried in vacuo to give the desired product.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate/brine (2×200 mL)
  2. concentrationIt was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-086b15eab19f456bacaf3a6b188d24cf
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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