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

HRID 76190Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([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:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:32][O:33][CH2:34][CH2:35][NH:36][CH3:37]>CN1C(=O)CCC1>[CH3:32][O:33][CH2:34][CH2:35][N:36]([CH3:37])[C:2]1[N:7]=[C:6]([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:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 31.4 mg (0.10 mmol) N-(1-(4-((2-chloropyrimidin-4-yl)ethynyl)phenyl)propan-2-yl)-acetamide (170) and 25.8 μl (0.15 mmol) DIPEA in 1 mL NMP are added 26.7 mg (0.30 mmol) N-(2-methoxyethyl)methylamine. The reaction mixture is stirred in a sealed tube at 120° C. over night and purified by HPLC (MeOH/H2O/TFA).

Workup

custompurified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record: ord-3871ce6d256e4f8fb42d77b2ca49aad3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Reaction notes

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