O-Phenylenediamine → HCID 136387965, compound

HRID 251675Notes

Reaction equation

HRID 251675 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[N:14][N:15]=[CH:16][C:17]1[NH:21][C:20]([CH3:22])=[C:19]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)=[O:24])[C:18]=1[CH3:34])([O-:3])=[O:2].Cl.C(N=C=NCCCN(C)C)C.O[C:48]1[C:56]2[N:55]=N[NH:53][C:52]=2[CH:51]=[CH:50][CH:49]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[N:14][N:15]=[CH:16][C:17]1[NH:21][C:20]([CH3:22])=[C:19]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:53][C:52]2[CH:51]=[CH:50][CH:49]=[CH:48][C:56]=2[NH2:55])=[O:33])=[O:24])[C:18]=1[CH3:34])([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136387966HCID 136387966, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 136387965HCID 136387965, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(5-(((5-nitro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid (468 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 (402 mg, 72% yield) as a red solid. LC-MS (m/z) 559 (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-7f77e5be8eb244489816471b39b8bdd9
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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