Ethanolamine → HCID 59242108, compound

HRID 1876184Notes

Reaction equation

HRID 1876184 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]([N+:22]([O-:24])=[O:23])[CH:8]=2)[N:3]=1.[CH2:25]([CH2:27][NH2:28])[OH:26]>CCCCO>[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]([N+:22]([O-:24])=[O:23])[CH:8]=3)[N:3]=[C:2]([NH:28][CH2:27][CH2:25][OH:26])[N:11]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11609884(2-Chloro-6-nitroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine

Product 1

HCID 59242108HCID 59242108, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 77 mg (0.22 mmol) of (2-chloro-6-nitro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine and 68 mg (1.12 mmol) of ethanolamine in n-BuOH was heated at 120° C. for 18 hours. The reaction mixture concentrated and the isolation was done by preparative HPLC to give the title compound. 1H NMR (DMSO-d6) δ 8.2-7.1 (7H), 3.83 (3H), 3.82 (s, 2H), 3.62 (d, 3H), 3.56 (s, 2H); LC-MS (ESI+; 294 ([M+H]+)).

Workup

  1. concentrationThe reaction mixture concentrated

Sources & evidence

ORD record
ord-ec4a5640df294418ba062c0adac7018f
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…