HCID 67381486, compound → HCID 178451891, compound

HRID 1470955Notes

Reaction equation

HRID 1470955 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=O>C(O)(=O)C.C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:9][C:3]=2[CH:4]=1

Participants

4

Reactant 1

HCID 67381486HCID 67381486, compound

Product 1

HCID 178451891HCID 178451891, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A solution of the compound of Example 49A in glatial acetic acid (75 mL) was warmed at 60° C. for 3 h. The mixture was cooled and diluted with toluene and concentrated in vacuo. The remainder of the acetic acid was removed by azeotroping with toluene (2×) and the residue was chromatographed over a 360 g silica gel cartridge, eluting with 25-75% ethyl acetate in dichloromethane. These procedures afforded the product (10.0 g, 85%) as a light beige rigid foam.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe remainder of the acetic acid was removed
  4. customby azeotroping with toluene (2×)
  5. customthe residue was chromatographed over a 360 g silica gel cartridge
  6. washeluting with 25-75% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-12a337d7ab9640099d05726c574deee3
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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