1,2-Dichloroethane → HCID 67496994, compound

HRID 1628339Notes

Reaction equation

HRID 1628339 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:3]1.[CH3:14][C:15]([O:18][C:19]([NH:21][C@H:22]([C:31](O)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:20])([CH3:17])[CH3:16].C(Cl)CCl>N1C=CC=CC=1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C@H:22]([NH:21][C:19](=[O:20])[O:18][C:15]([CH3:16])([CH3:14])[CH3:17])[C:31]([NH:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[CH:5]=2)=[O:32])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanineHCID 337835201-Methyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine

Product 1

HCID 67496994HCID 67496994, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 100 ml flask was added 1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine 17.B (540 mg, 3.10 mmole), Boc-L-4-fluorophenylalanine (970 mg, 3.41 mmole), EDC (710 mg, 3.72 mmole), and 10 ml of pyridine. The reaction was stirred at room temperature for 5.5 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 103.1.A (1.35 g, 99% yield) as colorless amorphous.

Workup

  1. customwas removed by rotary evaporation
  2. washwashed successively with saturated sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8b075205a83a475387d4f88b5acbb5ae
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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