Dodecylamine → HCID 68409673, compound

HRID 642137Notes

Reaction equation

HRID 642137 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[C:5]([C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:15]([NH2:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:15]([NH:27][C:12]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[NH:3][C:2](=[O:1])[C:10]2=[O:11])=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 13583DodecylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27793832,3-dioxoindoline-7-carboxylic acid

Product 1

HCID 68409673HCID 68409673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 2,3-dioxo-7-indolinecarboxylic acid (1000 mg, 5.23 mmol), 1-dodecanamine (1066 mg, 5.75 mmol), TEA (1.60 mL, 11.51 mmol), EDCI.HCl (1102 mg, 5.75 mmol) and HOBt (777 mg, 5.75 mmol) in DMF (60 mL). The resulting mixture was allowed to stir at rt for 24 hrs. The solvent was evaporated off and the residue was taken up in DCM to be purified by flash chromatography using DCM/MeOH (98/2) as eluant. A gummy orange solid was collected to be identified as the title compound (44%) in a 96.0% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customThe solvent was evaporated off
  2. customto be purified by flash chromatography
  3. customA gummy orange solid was collected

Sources & evidence

ORD record
ord-7075f76b6ddd4386ad90cf96f2da69f9
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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