Hydrochloric Acid → HCID 178465663, compound

HRID 421867Notes

Reaction equation

HRID 421867 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].CCN(CC)CC.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[C:24]([C:32]([NH:34][NH2:35])=[O:33])=[CH:25][N:26]([CH3:31])[C:27](=[O:30])[C:28]=2[F:29])=[C:18]([F:36])[CH:17]=1.Cl>CN(C=O)C.C1COCC1>[NH:7]=[C:2]([NH:35][NH:34][C:32]([C:24]1[C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][C:18]=2[F:36])=[C:28]([F:29])[C:27](=[O:30])[N:26]([CH3:31])[CH:25]=1)=[O:33])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 666737984-(4-Bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide

Product 1

HCID 178465663HCID 178465663, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl acetimidate HCl salt (40 mg, 0.32 mmol) and Et3N (0.049 mL, 0.35 mmol) were added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide (0.10 g, 0.27 mmol) in 2:1 THF:DMF (3 mL) at 0° C. After 1.5 hours at 0° C. and 17 hours at room temperature, the reaction mixture was poured onto water, neutralized with dilute aqueous HCl and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Trituration with methylene chloride gave the desired product.

Workup

  1. customat 0° C
  2. addition17 hours at room temperature, the reaction mixture was poured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19ddef6dd35a4042a799c2da1b9a9c9e
Source dataset
uspto-grants-2012_01
Patent number
US08101611B2

Reaction notes

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