Triethylamine → 8-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)octanoic acid methyl ester

HRID 251687

Reaction equation

HRID 251687 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=[N:12][N:13]=[CH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:54][O:55][C:56](=[O:65])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][NH2:64]>[Cl-].[Na+].O.CN(C=O)C>[CH3:54][O:55][C:56](=[O:65])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][NH:64][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([CH:14]=[N:13][N: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:16][CH:17]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12878164Methyl 8-aminooctanoate hydrochlorideHCID 1363879774-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 1363879818-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)octanoic acid methyl esterYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzoic acid (311 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 8-aminocaprylic acid methyl ester hydrochloride (251 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 (290 mg, 62% yield) as a brown solid. LC-MS (m/z) 467 (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-47efe2e26a774087b014fb3c6a9384e7
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Linked notes

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