Diisopropylethylamine → N-(1-(4-((2-((2-Methoxyethyl)(methyl)amino)pyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76192Notes

Reaction equation

HRID 76192 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[CH3:23][O:24][CH2:25][CH2:26][NH:27][CH3:28].CCN(C(C)C)C(C)C>CS(C)=O>[CH3:23][O:24][CH2:25][CH2:26][N:27]([CH3:28])[C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:12][CH:11]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 86669620N-(1-(4-((2-Chloropyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

Product 1

HCID 66614556N-(1-(4-((2-((2-Methoxyethyl)(methyl)amino)pyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

28.2 mg (0.09 mmol) N-(1-(4-((2-chloropyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)-acetamide (I69.1) in 1.5 mL DMSO are added to 12.0 mg (0.14 mmol) N-(2-methoxyethyl)-methylamine followed by 21.8 μl (0.14 mmol) DIPEA. The reaction mixture is stirred at r.t. over night and is directly purified by HPLC (MeOH/H2O/TFA).

Workup

  1. customis directly purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-730f548fa70541aebc007762dab2597c
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…