N,N-Dimethylglycine → HCID 58611972, compound

HRID 751291Notes

Reaction equation

HRID 751291 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[Br:29][C:30]1[CH:31]=[C:32]2[C:37](=[N:38][CH:39]=1)[N:36]=[C:35]([NH2:40])[CH:34]=[CH:33]2>C(Cl)Cl>[Br:29][C:30]1[CH:31]=[C:32]2[C:37](=[N:38][CH:39]=1)[N:36]=[C:35]([NH:40][C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH:34]=[CH:33]2

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 123488906-Bromo-1,8-naphthyridin-2-amine

Product 1

HCID 58611972HCID 58611972, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add N,N-dimethylglycine (0.28 g, 2.68 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (0.47 g, 2.45 mmol), 1-hydroxybenzotriazole (0.33 g, 2.45 mmol), and methylene chloride (111 mL) to 6-bromo-[1,8]naphthyridin-2-ylamine (Reichardt, C. et al, Tetrahedron Lett. 1977, 2087; 0.50 g, 2.23 mmol). Stir the reaction at room temperature for 19 h, concentrate in vacuo and purify by flash column chromatography to provide the subtitled compound (0.41 g, 60%) as an orange solid. MS ESI+ m/e 309/311 (M+1). 1H NMR (DMSO-d6) δ 10.52 (m, 1H), 8.96 (m, 1H), 8.71 (m, 1H), 8.35 (m, 2H), 3.15 (s, 2H), 2.25 (s, 6H). TLC (SiO2): Rf0.3 (1:4 [80:18:2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Workup

  1. customthe reaction at room temperature for 19 h
  2. concentrationconcentrate in vacuo
  3. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-adbfec10fa204b3b899503605c246c29
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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