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3,5-Dimethoxybenzaldehyde → [8-Benzyloxy-2-(3,5-dimethoxyphenyl)-imidazo[1,2-a]pyridin-3-ylamino]-acetic acid methyl ester

HRID 22795
Notes
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Reaction equation

HRID 22795 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])#[C-:17].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1)[CH:28]=O>Cl(O)(=O)(=O)=O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][NH:16][C:17]1[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:2]2=[N:1][C:28]=1[C:27]1[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:25]([O:24][CH3:23])[CH:26]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 817473,5-DimethoxybenzaldehydeHCID 903342-Amino-3-benzyloxypyridineHCID 547815Methyl isocyanoacetate

Product 1

HCID 69731334[8-Benzyloxy-2-(3,5-dimethoxyphenyl)-imidazo[1,2-a]pyridin-3-ylamino]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidSolvent

Procedure

Compound (9) was prepared according to the general synthesis instructions from 1.0 ml of 2-amino-3-benzyloxypyridine solution (0.1 M, DCM), 0.575 ml of methyl isocyanoacetate solution (0.2 M, DCM), 0.500 ml of 3,5-dimethoxybenzaldehyde solution (0.3 M, DCM), and 10 μl of perchloric acid (w=20%).

Sources & evidence

ORD record
ord-c1a9efe4ec324f5ca9ac07f17e534daa
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849642B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes