Ammonia → HCID 19808472, compound

HRID 373802Notes

Reaction equation

HRID 373802 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

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 19808485HCID 19808485, compound

Product 1

HCID 19808472HCID 19808472, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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°-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

  1. temperatureis maintained at -20°-20° C
  2. additionWhen the addition
  3. customThe organic phase, separated after settling
  4. dry with materialis dried over anhydrous magnesium sulfate
  5. customthe solvent evaporated off under vacuum
  6. dissolutionthe residue is dissolved in 20 ml of ethanol
  7. customthe hydrochloride is precipitated
  8. additionby adding 0.4 ml of 6N ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-f83b61f9ad0342e4b1ddb280e9395263
Source dataset
uspto-grants-1992_11
Patent number
US05166157

Reaction notes

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