Triethylamine → 6-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid methyl ester

HRID 251696Notes

Reaction equation

HRID 251696 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:61])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][NH2:60]>[Cl-].[Na+].O.CN(C=O)C>[CH3:52][O:53][C:54](=[O:61])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][NH:60][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 11499324Methyl 6-aminohexanoate hydrochlorideHCID 690330663-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690319736-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid methyl esterYield 81%

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 6-aminocaproic acid methyl ester hydrochloride (219 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 (332 mg, 81% yield) as a brown solid. LC-MS (m/z) 411 (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-f6c4fcb9254446ff855ad99595fc6fa1
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

Loading…