O-Phenylenediamine → 6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-aminophenyl)hexanamide

HRID 251698Notes

Reaction equation

HRID 251698 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:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:17].Cl.C(N=C=NCCCN(C)C)C.O[C:43]1[C:51]2[N:50]=N[NH:48][C:47]=2[CH:46]=[CH:45][CH:44]=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:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:48][C:47]1[CH:46]=[CH:45][CH:44]=[CH:43][C:51]=1[NH2:50])=[O:25])=[O:17]

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690325116-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690336266-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-aminophenyl)hexanamideYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid (396 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 (379 mg, 78% yield) as a brown solid. 1H NMR (DMSO-d6)δ1.36 (m, 2H, CH2), 1.59 (m, 4H, CH2), 2.30 (t, J=8.0 Hz, 2H, CH2CO), 3.29 (t, J=8.0 Hz, 2H, NCH2), 4.80 (s, 2H, benzene-NH2), 6.50 (t, J=8.0 Hz, 1H, Ar—H), 6.69 (d, J=8.0 Hz, 1H, Ar—H), 6.87 (m, 2H, Ar—H), 7.12 (m, 2H, Ar—H), 7.54 (d, J=8.0 Hz, 1H, Ar—H), 7.64 (m, 1H, Ar—H), 7.73 (s, 0.6 H, vinyl-H), 7.83 (m, 1H, Ar—H), 7.94 (m, 1H, Ar—H), 8.15 (s, 0.4 H, vinyl-H), 8.57 (m, 1H, Ar—H), 9.08 (s,1H, benzene-NH), 10.68 (s, 1H, CONH). LC-MS (m/z) 487 (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-aea00ae698394b4da083e6abfcdd32f7
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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