1-Hydroxybenzotriazole → HCID 11706659, compound

HRID 551935Notes

Reaction equation

HRID 551935 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=2[CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:27][C:28]1([CH3:42])[O:33][C:32]2[CH:34]=[CH:35][C:36]([C:38]([OH:40])=O)=[CH:37][C:31]=2[C:30](=[O:41])[O:29]1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=2[CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:38]([C:36]2[CH:35]=[CH:34][C:32]3[O:33][C:28]([CH3:27])([CH3:42])[O:29][C:30](=[O:41])[C:31]=3[CH:37]=2)=[O:40])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57554480N-{2-[(4-butylphenyl)ethynyl]benzyl}-1-hexanamineHCID 575544892,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxylic acid

Product 1

HCID 11706659HCID 11706659, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-{2-[(4-butylphenyl)ethynyl]benzyl}-1-hexanamine (174 mg, 0.50 mmol), 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxylic acid (122 mg, 0.55 mmol), EDC.HCl (115 mg, 0.60 mmol), DIEA (102 μl, 0.60 mmol) and HOBT (81 mg, 0.60 mmol) in DCM (10 mL) was stirred at rt for 3 hrs. The reaction mixture was diluted with DCM and washed with a saturated aqueous solution of NaHCO3, an aqueous solution of HCl (1N) and brine. The organic layer was dried over MgSO4 and the solvent Was removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (20/80)) gave 238 mg (87%) of the title compound. HPLC, Rt: 6.14 min (purity: 86.7%).

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent Was removed under reduced pressure
  4. customPurification by flash chromatography on silicagel (EtOAc/c-Hex (20/80))

Sources & evidence

ORD record
ord-27d98cd59e22490ca635f05b78ee6c2a
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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