Dimethylformamide → HCID 86596764, compound

HRID 1816055Notes

Reaction equation

HRID 1816055 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17]C(OC(C)(C)C)=O)=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:25]([C:32]1NC=CN=1)([C:27]1NC=CN=1)=[O:26].CN(C)[CH:39]=[O:40].[C:42]12([CH2:52][NH2:53])[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]3)[CH2:43]1)[CH2:49]2.[C:54](OCC)(=O)C>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:17])[C:39](=[O:40])[O:26][C:25]([CH3:32])([CH3:54])[CH3:27])=[CH:7][C:3]=1[C:4]([NH:53][CH2:52][C:42]12[CH2:49][CH:48]3[CH2:47][CH:46]([CH2:45][CH:44]([CH2:50]3)[CH2:43]1)[CH2:51]2)=[O:6]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21900010HCID 21900010, compound

Product 1

HCID 86596764HCID 86596764, compound

Procedure

2-Chloro-5-[[3-[[(1,1-dimethylethoxy)carbonyl]methylamino]propoxy]methyl]-benzoic acid (0.318 g, Example 23a), carbonyl diimidazole (0.165 g) and dimethylformamide (10 ml) were heated at 50° C. under nitrogen for 30 min. The mixture was allowed to cool to room temperature and 1-adamantanemethylamine (0.18 ml) was added. The mixture was stirred at room temperature for 20 h then poured into ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate solution followed by brine. The solution was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (eluting with 2:1 isohexane/ethyl acetate) to afford the subtitled compound (0.236 g).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (eluting with 2:1 isohexane/ethyl acetate)

Sources & evidence

ORD record
ord-8b13d2d74bd14efebf0e2a7935eae94b
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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