Hydrochloric Acid → HCID 178517793, compound

HRID 1403082Notes

Reaction equation

HRID 1403082 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:12]([I:13])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7].[F:14][C:15]([F:22])([F:21])[C:16](OCC)=O.Cl>C(O)C.O>[I:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:5]2[C:4]=1[NH:3][C:16]([C:15]([F:22])([F:21])[F:14])=[N:8][C:6]2=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 674974502-Amino-3-iodobenzamide

Product 1

HCID 178517793HCID 178517793, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

EDCI hydrochloride (18.4 g) and 1-hydroxybenzotriazole (9.5 g) were added to a solution of 2-amino-3-iodobenzoic acid (16.4 g) synthesized using the method described in Journal of Medicinal Chemistry, 2004, 47 (6), 1448-1464 in DMF (120 mL), and subsequently ammonia water (21.2 ml) was added thereto. The reaction solution was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the deposit was filtrated and dried under reduced pressure to obtain 2-amino-3-iodobenzamide (12.8 g). 60% sodium hydride (2.29 g) was added to a solution of the obtained 2-amino-3-iodobenzamide (5.0 g) in ethanol (95 ml), then ethyl trifluoroacetate (10.8 g) was added thereto, and the mixture was heated to reflux for 15 hours. After cooling, water was added thereto, and the reaction solution was rendered acidic by the addition of 6 N hydrochloric acid. Then, the deposit was filtrated and dried under reduced pressure to obtain compound (4a) (6.4 g, yield based on 2 steps: 77%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 hours
  3. temperatureAfter cooling
  4. filtrationThen, the deposit was filtrated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7af9b919a14148eda88b6c9d64c61fa9
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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