HCID 22222598, compound → HCID 22222626, compound

HRID 1794692Notes

Reaction equation

[CH:1]([O:4][C:5]([O:7][CH2:8][N:9]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]([C:19](=[O:33])[C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:21]=2[N+:30]([O-])=O)=[N:10]1)=[O:6])([CH3:3])[CH3:2].C(OC(N1N=C(C(OCC)=O)C(C(=O)C2C=C(OC)C(OC)=CC=2[N+]([O-])=O)=N1)=O)(C)C>>[NH2:30][C:21]1[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:20]=1[C:19]([C:11]1[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:13][N:9]([CH2:8][O:7][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:6])[N:10]=1)=[O:33]

Participants

Reactant 2

HCID 22222598HCID 22222598, compound

HCID 22222638HCID 22222638, compound

Product 1

HCID 22222626HCID 22222626, compoundYield 75.2%

Procedure

The 2:1 mixture (870 mg) of ethyl 2-(isopropoxycarbonyloxymethyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate and ethyl 2-(isopropoxycarbonyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate prepared in step (7a) was reacted in the same manner as in Example 3 (3a). The reaction product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give a 4:1 mixture (612 mg) of ethyl 5-(2-amino-4,5-dimethoxybenzoyl)-2-(isopropoxycarbonyloxymethyl)-2H-1,2,3-triazole-4-carboxylate and ethyl 5-(2-amino-4,5-dimethoxybenzoyl)-2-(isopropoxycarbonyl)-2H-1,2,3-triazole-4-carboxylate as a light yellow foam.

Workup

customThe reaction product was purified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-0afcf9ef7ae143b5ab1cc45f8c379b85
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022860B2

Reaction notes

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