Diisopropylethylamine → n-[7-((Methanesulfonyl)oxy)naphthyl]-2-[n'-(2-(1-triphenylmethyl-4-imidazolyl)ethyl)amino]acetamide

HRID 412171Notes

Reaction equation

HRID 412171 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][NH2:15])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:38][C:39]([NH:41][C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([O:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:50]=2)[CH:45]=[CH:44][CH:43]=1)=[O:40]>C(#N)C>[CH3:56][S:53]([O:52][C:49]1[CH:50]=[C:51]2[C:46]([CH:45]=[CH:44][CH:43]=[C:42]2[NH:41][C:39](=[O:40])[CH2:38][NH:15][CH2:14][CH2:13][C:11]2[N:10]=[CH:9][N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:12]=2)=[CH:47][CH:48]=1)(=[O:55])=[O:54]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6183402-(1-Trityl-1H-imidazol-4-yl)-ethylamineHCID 155493251-(Chloroacetamido)-7-[(methanesulfonyl)oxy]naphthalene

Product 1

HCID 18536022n-[7-((Methanesulfonyl)oxy)naphthyl]-2-[n'-(2-(1-triphenylmethyl-4-imidazolyl)ethyl)amino]acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product from Step B (25.6 g, 72.7 mmol) in 200 mL of acetonitrile was added diisopropylethylamine (50 mL, 303 mmol), followed by the product from Step D (19.0 g, 60.5 mmol). The reaction was stirred at room temperature overnight, then concentrated in vacuo. The resulting material was partitioned between EtOAc and water, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting material was partitioned between EtOAc and water
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f4b809b1d22411c9cb661d6ae3361f0
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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