3,5-Diamino-2-methylbenzoic acid → HCID 135537135, compound

HRID 2182338Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[N:2]1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[NH2:23])[C:16]([O:18][CH3:19])=[O:17]>[N+](C1C=CC=CC=1)([O-])=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:12][C:13]3[CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:20]=[CH:21][C:22]=3[N:23]=2)=[N:2]1

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 0.1 g of 1H-indazole-3-carboxaldehyde and 113.7 mg of methyl 3,4-diaminobenzoate in 10 ml of nitrobenzene is maintained at a temperature in the region of 145° C. for 3 hours and 45 minutes. After cooling to a temperature in the region of 20° C., the reaction mixture is purified on SPE (5 g of SCX phase, processing and washing with methanol, extraction with a 2N ammoniacal methanol solution). The ammoniacal solution collected during the detachment is then concentrated under reduced pressure at a temperature in the region of 40° C. 198.3 mg of an orange lacquer are obtained and are purified by preparative LC-MS. 42.7 mg of methyl 2-(1H-indazol-3-yl)-3H-benzimidazole-5-carboxylate are thus obtained in the form of a beige-coloured powder, the characteristics of which are as follows:

Workup

temperatureAfter cooling to a temperature in the region of 20° C.
customthe reaction mixture is purified on SPE (5 g of SCX phase
washwashing with methanol, extraction with a 2N ammoniacal methanol solution)
customThe ammoniacal solution collected during the detachment
concentrationis then concentrated under reduced pressure at a temperature in the region of 40° C
custom198.3 mg of an orange lacquer are obtained
customare purified by preparative LC-MS

Sources & evidence

ORD record: ord-5b1e2fecdfee42409dfdf0fe6aeb1119
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897208B2

Reaction notes

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