Ethanolamine → HCID 59242100, compound

HRID 1876160Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=2)[N:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=3)[N:3]=[C:2]([NH:26][CH2:25][CH2:23][OH:24])[N:11]=2)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 113928514-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-N,6-dimethyl-

Product 1

HCID 59242100HCID 59242100, compoundYield 35%

Procedure

A solution of (2-chloro-6-methyl-quinazolin-4-yl)-(4-methoxyphenyl)-methyl-amine (50.3 mg, 0.16 mmol) in ethanolamine (1.5 mL) was heated to 140° C. in the microwave for 20 min. The reaction was then concentrated onto SiO2 and purified by gradient MPLC (SiO2, 0-100%, EtOAc/hexanes, 20 min). 19.1 mg (35%) of the title compound was isolated: 1H NMR (DMSO-d6) δ 7.33 (d, 1 H), 7.21 (dd, 1 H), 7.04-7.10 (m, 2H), 6.86-6.92 (m, 2H), 6.57-6.62 (m, 1H), 5.44 (br s, 1H), 3.82-3.94 (m, 2H), 3.83 (s, 3H), 3.62-3.67 (m, 2H), 3.48 (s, 3H), 2.01 (s, 3H). HRMS (ES) calcd for C19H23N4O2 [(M+H)] 339.1816, found 339.1854.

Workup

concentrationThe reaction was then concentrated onto SiO2
custompurified by gradient MPLC (SiO2, 0-100%, EtOAc/hexanes, 20 min)

Sources & evidence

ORD record: ord-2adf643859f742558f95feb3d020b27a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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