Triethylamine → HCID 58405839, compound

HRID 44834Notes

Reaction equation

HRID 44834 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[N:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:24])[C:8](=[O:25])[C@H:7]2[CH2:26][CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:29][N:30]=[C:31]=NCCCN(C)C.Cl.CNC.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([C:21]([N:30]([CH3:31])[CH3:29])=[O:23])[CH:18]=[N:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:24])[C:8](=[O:25])[C@H:7]2[CH2:26][CH3:27])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 58405385HCID 58405385, compound

Product 1

HCID 58405839HCID 58405839, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-1-(8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-pyrazole-4-carboxylic acid (Example 44, 0.14 g, 0.378 mmol) was dissolved in 2 mL of DCM and EDCI (79 mg, 0.415 mmol), dimethylamine hydrochloride (46 mg, 0.567 mmol), HOAt (5 mg, 0.0379 mmol) and triethylamine (115 mg, 1.13 mmol) were added. The resulting solution was stirred at rt for 48 hours after which the reaction mixture was diluted with DCM and washed with 0.1 N aqueous HCl then 1 N aqueous NaOH, dried with Na2SO4, filtered, concentrated under vacuum and purified by preparative HPLC to give the title compound. 1H NMR (CDCl3) δ: 7.55-7.57 (s, 1H), 7.40-7.51 (m, 2H), 4.26-4.51 (m, 2H), 3.11-3.39 (m, 9H), 1.64-2.18 (m, 10H), and 0.97 ppm (m, 3H); LCMS: 398.1 m/z (M+H)+; ret. Time: 3.267 min (Analytical Method A).

Workup

  1. washwashed with 0.1 N aqueous HCl
  2. dry with material1 N aqueous NaOH, dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-10bfc060e9c346db9ed4630cf55662d1
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

Loading…