Hydrochloric Acid → HCID 59199417, compound

HRID 2089530Notes

Reaction equation

Cl.[CH3:2][O:3][C:4]([C:6]1[N:7]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](O)([CH3:21])[CH2:13][C:12]2([CH3:24])[CH3:23])[CH:8]=[N:9][CH:10]=1)=[O:5]>CO>[CH3:2][O:3][C:4]([C:6]1[N:7]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH3:21])=[CH:13][C:12]2([CH3:24])[CH3:23])[CH:8]=[N:9][CH:10]=1)=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 1.25 M anhydrous methanol solution of HCl (3 mL) is added 3-(4-hydroxy-2,2,4-trimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester, which can be prepared as described in Example 38, (85 mg, 0.27 mmol). The reaction is then heated to 50° C., and is then concentrated to dryness. The resulting residue is purified by silica gel flash chromatography (diethylamine-methanol-dichloromethane, 0.5:1:98.5) to provide 3-(2,2,4-trimethyl-1,2-dihydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 297.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.86 (s, 3 H), 1.13 (s, 3 H), 2.15 (d, J=1.3 Hz, 3 H), 3.91 (s, 3 H), 5.56 (s, 1 H), 6.31 (s, 1 H), 7.16-7.26 (m, 2 H), 7.31-7.41 (m, 2 H), 7.43 (s, 1 H), 7.70 (s, 1 H). The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to afford the HCl salt of 3-(2,2,4-trimethyl-1,2-dihydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester.

Workup

customcan be prepared
concentrationis then concentrated to dryness
customThe resulting residue is purified by silica gel flash chromatography (diethylamine-methanol-dichloromethane, 0.5:1:98.5)

Sources & evidence

ORD record: ord-99bb2b2f88654c98afe3b2c912fff6f7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436035B2

Reaction notes

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