O-Phenylenediamine → 5-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-aminophenyl)pentanamide

HRID 251703Notes

Reaction equation

HRID 251703 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:26]=[CH:27][CH:28]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[O:17].Cl.C(N=C=NCCCN(C)C)C.O[C:42]1[C:50]2[N:49]=N[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[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:26]=[CH:27][CH:28]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:47][C:46]1[CH:45]=[CH:44][CH:43]=[CH:42][C:50]=1[NH2:49])=[O:25])=[O:17]

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690319325-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690327205-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-aminophenyl)pentanamideYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid (382 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (432 mg, 4 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 (382 mg, 81% yield) as a brown solid. LC-MS (m/z) 473 (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-e06b66ee7dd84be5a317d6cfff0fd356
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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