Ammonia → HCID 19808472, compound

HRID 373812Notes

Reaction equation

[ClH:1].C[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:16][CH2:15]1)=[CH:9][CH:8]=[CH:7]2.B(Br)(Br)Br.N>ClCCl>[ClH:1].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][C:23](=[O:31])[C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH2:16][CH2:15]1)=[CH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 0.85 g of the compound of Example 1, in base form, in 40 ml of dichloromethane is cooled to -20° C. under a nitrogen atmosphere. 10 ml of a molar solution of boron tribromide in dichloromethane are then added dropwise while the temperature is maintained at -20° C. When the addition is complete, the medium is slowly heated to room temperature and stirred at this temperature for one hour before being hydrolyzed with 2 ml of ammonia solution. The organic phase, separated after settling has taken place, is dried over anhydrous magnesium sulfate and the solvent evaporated off under vacuum; the residue is dissolved in 20 ml of ethanol and the hydrochloride is precipitated by adding 0.4 ml of 6N ethanolic hydrogen chloride.

Workup

additionWhen the addition
temperaturethe medium is slowly heated to room temperature
customThe organic phase, separated after settling
dry with materialis dried over anhydrous magnesium sulfate
customthe solvent evaporated off under vacuum
dissolutionthe residue is dissolved in 20 ml of ethanol
customthe hydrochloride is precipitated
additionby adding 0.4 ml of 6N ethanolic hydrogen chloride

Sources & evidence

ORD record: ord-79cf37a7b41a44bea54d1ebd09751d5f
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166156

Reaction notes

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