Triethylamine → 5-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid methyl ester

HRID 251701

Reaction equation

HRID 251701 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](O)=[O:17].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:52][O:53][C:54](=[O:60])[CH2:55][CH2:56][CH2:57][CH2:58][NH2:59]>[Cl-].[Na+].O.CN(C=O)C>[CH3:52][O:53][C:54](=[O:60])[CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([CH:12]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][C:6]2=[O:11])[CH:14]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13672034Methyl 5-aminopentanoate hydrochlorideHCID 690330663-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690347625-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid methyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzoic acid (283 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 5-aminovaleric acid methyl ester hydrochloride (202 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (337 mg, 89% yield) as a brown solid. LC-MS (m/z) 397 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-396d68cdaffe4c38868c21886558fa6a
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Linked notes

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