N,N-Dimethylethylenediamine → HCID 18617690, compound

HRID 1264248Notes

Reaction equation

HRID 1264248 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][N:18]([CH2:20][CH2:21][NH2:22])[CH3:19]>CS(C)=O>[CH3:17][N:18]([CH3:19])[CH2:20][CH2:21][NH:22][C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 186174554-(2-Chloro-4-pyrimidinyl)benzoic acid

Product 1

HCID 18617690HCID 18617690, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-[2-chloro-pyrimidin-4-yl]-benzoic acid (234 mg, 1 mmol, reference example 11 g) in DMSO (2 mL) is added 2-(N,N-dimethyl-amino)ethylamine (291 mL, 2 mmol). The resulting solution is heated to 85° C. and stirred at this temperature for 3.5 hours, then cooled and concentrated. The residue is purified by reverese phase HPLC to give 296 mg of the title compound as a TFA salt. 1H NMR (CD3OD) d 2.97 (s, 6H), 3.45 (t, J=6 Hz, 2H), 3.88 (t, J=6 Hz, 2H), 7.31 (d, J=5 Hz, 1H), 8.13 (d, J=8 Hz, 2H), 8.20 (d, J=8 Hz, 2H), 8.44 (d, J=5 Hz, 1H). MS (ion spray) m/z 286 (M+).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue is purified by reverese phase HPLC

Sources & evidence

ORD record
ord-e43215fd5c7d49e3990da1d208cc861b
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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