Dimethylformamide → HCID 86742915, compound

HRID 620287Notes

Reaction equation

HRID 620287 reaction equation
N[C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[O:7])=[C:4]([OH:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]#[CH:29].C[N:32](C=O)C>C1(C)C=CC=CC=1>[NH2:32][C:3]1[C:4]([O:20][CH2:27][C:28]#[CH:29])=[C:5]([CH:17]=[C:18]([Cl:19])[CH:2]=1)[C:6]([NH:8][CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromide2×HCID 11430Potassium CarbonateHCID 156708204-Amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-hydroxybenzamide

Product 1

HCID 86742915HCID 86742915, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-N-(1-azabicyclo[2.2.2]-oct-3-yl)-5-chloro-2-hydroxybenzamide (590 mg), potassium carbonate (2.8 g), propargyl bromide (9.3 g of an 80% solution of propargyl bromide in toluene) in DMF (10 mL) was stirred at room temperature for 1 hour. The solid was filtered off, and the filtrate diluted with ether. The resulting precipitate was collected and washed with ether. This solid was dissolved in a small amount of a mixture of acetonitrile, methanol and ammonium hydroxide in the ratio of 100:15:0.5, and flash chromatographed over silica gel eluting with the same solvent system. The appropriate fractions were combined and concentrated. The resulting solid was dried under vacuum to yield the title compound (0.115 g; 17%), m.p. >170° C. decomp.

Workup

  1. filtrationThe solid was filtered off
  2. additionthe filtrate diluted with ether
  3. customThe resulting precipitate was collected
  4. washwashed with ether
  5. dissolutionThis solid was dissolved in a small amount of a mixture of acetonitrile, methanol and ammonium hydroxide in the ratio of 100:15:0.5, and flash
  6. customchromatographed over silica gel eluting with the same solvent system
  7. concentrationconcentrated
  8. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-31713927846f41b3aa101c4fcc6352f4
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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