Ethanolamine → [4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][4-(2-hydroxyethyl)amino-3-nitrophenyl]methanone

HRID 10803

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)=[O:8].[CH2:33]([CH2:35][NH2:36])[OH:34].C(N(CC)C(C)C)(C)C>C(O)CCC>[NH2:1][C:2]1[N:3]=[C:4]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:36][CH2:35][CH2:33][OH:34])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone (of Example 15; 0.25 g, 0.53 mmol), ethanolamine (0.13 mL, 2.12 mmol), N,N-diisopropylethylamine (Aldrich) (0.37 mL, 2.12 mmol) in n-butanol (10 mL) was heated at 100° C. overnight. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel using MeOH/CH2Cl2 (1/9) as the eluent to afford 73 mg (28% yield) of the title compound. Mass spectrum (ES) MH+=498.

Workup

customThe solvent was evaporated in vacuo
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-514f448472b6432cb9ba9c7ab9748ad1
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094896B2

Linked notes

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