Ethanolamine → HCID 44468322, compound

HRID 1366109Notes

Reaction equation

HRID 1366109 reaction equation
[CH3:1][C:2]1[C:3](=[O:29])[N:4]([CH2:24][CH2:25][C:26]([OH:28])=O)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[CH:6]=2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:52]([CH2:54][NH2:55])[OH:53]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[OH:53][CH2:52][CH2:54][NH:55][C:26](=[O:28])[CH2:25][CH2:24][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[CH:6]=2)[N:11]=[C:2]([CH3:1])[C:3]1=[O:29]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59822528HCID 59822528, compound

Product 1

HCID 44468322HCID 44468322, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

In this example 3-(3-methyl-2-oxo-7-(3-(trifluoromethyl)benzylamino)-quinoxalin-I (2H)-yl)propanoic acid (50 mg) was dissolved in chloroform (1 mL). HOBt (20 mg), EDC hydrochloride (29 mg), triethylamine (75 μL), and ethanolamine (9 μL) were added sequentially to the reaction flask and stirred overnight. Concentrated and residue chromatographed on silica gel using 5% MeOH in dichloromethane as eluent. Product N-(2-hydroxyethyl)-3-(3-methyl-2-oxo-7-(3-(trifluoromethyl)benzylamino)-quinoxalin-1(2H)-yl)propanamide is isolated as yellow solid.

Workup

  1. concentrationConcentrated
  2. customresidue chromatographed on silica gel using 5% MeOH in dichloromethane as eluent

Sources & evidence

ORD record
ord-435d64e06c674fa590c4428e12e1facf
Source dataset
uspto-grants-2011_02
Patent number
US07893066B2

Reaction notes

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