1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58597275, compound

HRID 1444731Notes

Reaction equation

HRID 1444731 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].[NH2:22][CH:23]1[CH2:32][CH2:31][CH2:30][C:29]2[N:28]=[C:27]([CH2:33][CH2:34]O)[N:26]=[CH:25][C:24]1=2.[CH:36]1[CH:37]=[CH:38]C2N(O)N=[N:42][C:40]=2[CH:41]=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:10])=[O:9])[C@@H:3]1[CH2:18][C:19]([NH:22][CH:23]1[CH2:32][CH2:31][CH2:30][C:29]2[N:28]=[C:27]([CH2:33][CH2:34][N:42]3[CH2:38][CH2:37][CH2:36][CH2:41][CH2:40]3)[N:26]=[CH:25][C:24]1=2)=[O:20]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 588413542-(5-Amino-5,6,7,8-tetrahydroquinazolin-2-yl)ethanolHCID 59167870(R)-2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetic acid

Product 1

HCID 58597275HCID 58597275, compound

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 (1.55 g, 5.0 mmol), crude 2-(5-amino-5,6,7,8-tetrahydroquinazolin-2-yl)ethanol (966 mg, 5.0 mmol), HOBT (676 mg, 5.0 mmol) and EDCI (959 mg, 5.0 mmol) in 2.5 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 100:25 to 100:30) gave the desired product as a white solid. MS: 486.2 (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-da6edf5f83ae4f6e9f5c879138554420
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…