1-Hydroxybenzotriazole → N-(1-methyl-1-methoxyethoxy)-3-(5-(2-(2-(4-methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanamide

HRID 1353151Notes

Reaction equation

HRID 1353151 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH2:18][CH2:19][CH:20]=[C:21]4[CH2:26][CH2:27][C:28](O)=[O:29])[N:12]=2)=[CH:4][CH:3]=1.[NH2:32][O:33][C:34]([O:37][CH3:38])([CH3:36])[CH3:35].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(N(CC)CC)C.CN(C)C=O>[CH3:35][C:34]([O:37][CH3:38])([O:33][NH:32][C:28](=[O:29])[CH2:27][CH2:26][C:21]1[C:22]2[C:17](=[C:16]([O:15][CH2:14][CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)[O:9][C:10]=3[CH3:31])[CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:19][CH:20]=1)[CH3:36]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 99098753-(5-(2-(2-(4-Methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanoic acidHCID 13608208O-(2-Methoxyisopropyl)hydroxylamine

Product 1

HCID 23157991N-(1-methyl-1-methoxyethoxy)-3-(5-(2-(2-(4-methylphenyl)-5-methyloxazol-4-yl)ethoxy)-3,4-dihydronaphthalen-1-yl)propanamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a dimethylformamide (5 ml) solution of the compound (208 mg) prepared in Example 2 and 2-aminooxy-2-methoxypropane (57.7 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg), 1-hydroxybenzotriazole (81 mg) and triethylamine (83 μl ) were added, followed by stirring at room temperature overnight. The reaction mixture was concentrated. The residue was diluted with methylene chloride. The diluted solution was washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to thereby obtain the title compound (239 mg) having the following physical data.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with methylene chloride
  3. washThe diluted solution was washed with 1N hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order, dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-bdfc4b3669f04e64860688dc33a15b4b
Source dataset
uspto-grants-2007_05
Patent number
US07220864B2

Reaction notes

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