Hydrochloric Acid → HCID 22185475, compound

HRID 1795143Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:24]C.B(Br)(Br)Br.Cl.[OH-].[Na+]>ClCCl.O>[NH2:21][CH2:20][C:19]([C:10]1[NH:11][C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([OH:24])[CH:4]=2)[N:9]=1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of Example 2 (356 mg, 1 mmol) in dichloromethane (20 ml) cooled to 5° C. was treated with boron tribromide (1M in dichloromethane, 5 ml) followed by additional dichloromethane (10 ml). The solution was stirred at 5° C. for 2 hours then at room temperature for a further 2 hours. 2M hydrochloric acid (1 ml) and water (5 ml) were then added and the reaction heated to 50° C. for 15 min. After cooling the mixture was neutralised with 15% sodium hydroxide solution and the resultant precipitate collected by filtration to afford the title compound as a yellow solid (206 mg, 60%); MS(ES+) m/e 343/345 [M+H]+.

Workup

waitat room temperature for a further 2 hours
temperaturethe reaction heated to 50° C. for 15 min
temperatureAfter cooling the mixture
filtrationthe resultant precipitate collected by filtration

Sources & evidence

ORD record: ord-95e10c29235c441b9bc9fd251c920326
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026336B1

Reaction notes

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