O-Phenylenediamine → 5-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-aminophenyl)pentanamide

HRID 1926188Notes

Reaction equation

HRID 1926188 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.O[C:38]1[C:46]2[N:45]=N[NH:43][C:42]=2[CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:43][C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:46]=3[NH2:45])=[O:23])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579720655-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 445402515-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-aminophenyl)pentanamideYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid (321 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), hydroxy-benzotriazole (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 (292 mg, 71% yield) as a brown solid. LC-MS (m/z) 412 (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-1c9249842a7c453f857decca28ef150e
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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