N,N-Dimethylglycine → HCID 58739187, compound

HRID 720267Notes

Reaction equation

HRID 720267 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([OH:7])=O)[CH3:3].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[C:16]([C@@H:20]([NH2:22])[CH3:21])[CH:17]=[CH:18][CH:19]=2)[CH:9]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([NH:22][C@H:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:10]2[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=2)[CH:15]=1)[CH3:21])=[O:7]

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57419702HCID 57419702, compound

Product 1

HCID 58739187HCID 58739187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of dimethylamino-acetic acid (0.083 mmol), (S)-1-(3-pyridin-3-yl-phenyl)-ethylamine (12.7 mg, 0.064 mmol), EDAC.HCl (18.4 mg, 0.096 mmol), HOBT (13 mg, 0.096 mmol) and diisopropylethylamine (33 μL, 0.192 mmol) in DMF (2 mL) was stirred at room temperature for 18 h, and the reaction mixture was purified by preparative HPLC (5 mM NH4OAc buffer; gradient 0% to 100% B in 10 min (A: 10% CH3CN/H2O ; B: 90% CH3CN/H2O; column: Primesphere C18 HC 21.2×100 mm) to afford the title product.

Workup

  1. customthe reaction mixture was purified by preparative HPLC (5 mM NH4OAc buffer
  2. waitgradient 0% to 100% B in 10 min (A: 10% CH3CN/H2O

Sources & evidence

ORD record
ord-34853534d8ab4a078a3cf18a4c869b60
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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