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

HRID 1795098Notes

Reaction equation

HRID 1795098 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-f5a51818adf047139f307870489f4aa7
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

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