Hydrochloric Acid → N-(6-Chloro-9H-beta-carbolin-8-yl)-3,4-difluoro-benzamide

HRID 1168736Notes

Reaction equation

HRID 1168736 reaction equation
N[N:2]1[C:14]2[CH:13]=[N:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](Cl)=[CH:6][CH:7]=2.[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[F:26])[C:20](Cl)=O.[OH-:27].[Na+].[ClH:29].[N:30]1C=CC=CC=1>O>[Cl:29][C:6]1[CH:7]=[C:8]2[C:3](=[C:4]([NH:30][C:20](=[O:27])[C:19]3[CH:23]=[CH:24][C:25]([F:26])=[C:17]([F:16])[CH:18]=3)[CH:5]=1)[NH:2][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14798Sodium HydroxideHCID 27245193,4-Difluorobenzoyl chlorideHCID 221852799-Amino-7-chloro-beta-carboline

Product 1

HCID 22185231N-(6-Chloro-9H-beta-carbolin-8-yl)-3,4-difluoro-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a cold (3° C.-5° C.) solution of 9-amino-7-chloro-β-carboline (2.50 g, 11.5 mmol, as prepared in example 60 above) in pyridine (130 ml) was added 3,4-diflourobenzoyl chloride (1.67 ml, 13.25 mmol). The reaction was allowed to warm to RT and stirred for 20 h before diluting the reaction with water (60 ml) and 1M NaOH (15 ml). After stirring for 3 h at RT, the pH of the mixture was adjusted to 8-9 with 1M HCl and then poured into water (250 ml). The mixture was allowed to stand for 30 min and the product was filtered to provide 3.95 g of the title compound after washing with water and drying under reduced pressure at 55° C.-60° C.

Workup

  1. additionbefore diluting
  2. stirringAfter stirring for 3 h at RT
  3. waitto stand for 30 min
  4. filtrationthe product was filtered

Sources & evidence

ORD record
ord-58f3c225fd2c4bbdad24d2b5180a7a94
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

Loading…