Triethylamine → HCID 178509147, compound

HRID 2095188Notes

Reaction equation

HRID 2095188 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[N:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C:7]([NH2:10])=[N:8][N:9]=1.C(N(CC)CC)C.S(OCCOS(C1C=CC(C)=CC=1)(=O)=O)(C1C=CC(C)=CC=1)(=O)=O.[C:51]([O:54][CH2:55][CH3:56])(=O)[CH3:52]>CN(C=O)C>[F:19][C:15]1[CH:14]=[C:13]([NH:12][N:11]=[C:6]2[C:5]([CH2:4][CH2:3][CH2:2][N:1]3[CH2:56][CH2:55][O:54][CH2:51][CH2:52]3)=[N:9][N:8]=[C:7]2[NH2:10])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 228289Ethylene glycol ditosylateHCID 178510950HCID 178510950, compound

Product 1

HCID 178509147HCID 178509147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
96 °C

Procedure

A suspension of 5-(3-aminopropyl)-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine, obtained in Example 32, (400 mg, 1.53 mmole) and triethylamine (6 mmole) in 10 mL of DMF was heated to 96° C. To this solution was slowly added a solution of ethylene glycol ditosylate (3 mmole) in 10 mL DMF. The reaction was worked up by the addition of saline and ethyl acetate. The organic phase was separated, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography and further by preparative TLC. The resulting 34 mg of oil was dissolved in a minimum amount of diethyl ether and then mixed with hexanes to yield 22 mg of the title compound as a yellow powder. MS (m/z, ES+): 333 (M+1, 100%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography and further by preparative TLC
  6. dissolutionThe resulting 34 mg of oil was dissolved in a minimum amount of diethyl ether
  7. additionmixed with hexanes

Sources & evidence

ORD record
ord-67c73c486df1468aa16c7d492c473b02
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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