Water → HCID 22645702, compound

HRID 2414352Notes

Reaction equation

HRID 2414352 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].[Br:28][CH2:29][CH2:30][C:31](O)=[O:32].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:31](=[O:32])[CH2:30][CH2:29][Br:28])=[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 115533-Bromopropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10523682HCID 10523682, compound

Product 1

HCID 22645702HCID 22645702, compoundYield 27%

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 (1.51 g, 4.00 mmol) in dimethylformamide (40 mL) were added 3-bromopropionic acid (3.06 g, 20.0 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.83 g, 20.0 mmol), and the mixture was stirred at room temperature for 45 minutes. Water was added thereto and the mixture was extracted with ethyl acetate. Purification by silica gel column chromatography (6:1 chloroform/acetate) gave 7-(acetoxymethyl)-5-amino-2-[4-[(3-bromopropionyl)amino]-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one (554 mg, 27%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customPurification by silica gel column chromatography (6:1 chloroform/acetate)

Sources & evidence

ORD record
ord-7c75ef8e2c1a4531b5150ceb6d502775
Source dataset
uspto-grants-2004_11
Patent number
US06812246B2

Reaction notes

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