Water → HCID 12132659, compound

HRID 2414353Notes

Reaction equation

HRID 2414353 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:24]([F:25])=[C:23]([NH2:26])[C:9]2[C:10](=[O:22])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=3)[O:13][C:8]=2[C:7]=1[F:27])(=[O:3])[CH3:2].Cl.[CH3:29][N:30]([CH3:37])[CH2:31][CH2:32][CH2:33][C:34](O)=[O:35].Cl.CN(C)CCCN=C=NCC.O>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[C:24]([F:25])=[C:23]([NH2:26])[C:9]2[C:10](=[O:22])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][N:30]([CH3:37])[CH3:29])=[C:16]([F:21])[CH:15]=3)[O:13][C:8]=2[C:7]=1[F:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10523682HCID 10523682, compoundHCID 126916404-(Dimethylamino)butyric acid hydrochloride

Product 1

HCID 12132659HCID 12132659, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(acetoxymethyl)-5-amino-2-[4-amino-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one (500 mg, 1.32 mmol) in dimethylformamide (15 mL) were added 4-dimethylaminobutyric acid hydrochloride (3.06 g, 16.9 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.23 g, 16.9 mmol), and the mixture was stirred at room temperature for 2.5 hours. Water was added thereto, and the mixture was extracted with ethyl acetate. Purification by silica gel column chromatography (9:1 chloroform/methanol) gave 1j (386 mg, 60%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customPurification by silica gel column chromatography (9:1 chloroform/methanol)

Sources & evidence

ORD record
ord-1b424885fcff4808936d5de14ae63791
Source dataset
uspto-grants-2004_11
Patent number
US06812246B2

Reaction notes

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