P-Toluenesulfonylhydrazide → HCID 68512118, compound

HRID 2241342Notes

Reaction equation

HRID 2241342 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([C:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH:27]=3)=[N:9]2)=[CH:5][CH:4]=1.CC1C=CC(S(NN)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=4)[N:9]=[C:10]([CH:26]4[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:30][CH2:31]4)[C:11]=23)=[C:19]([F:25])[CH:20]=1

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 68516875HCID 68516875, compound

Product 1

HCID 68512118HCID 68512118, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL round-bottomed flask was charged with tert-butyl 4-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.248 g, 0.455 mmol), 4-methylbenzenesulfonohydrazide (0.0846 g, 0.455 mmol) and toluene (10 mL). The reaction mixture was stirred at 100° C. for 4 days. The reaction was cooled to ambient temperature and partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude material was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford the product (84.3 mg, 33.9%). LRMS (APCI pos): >96% purity, 254 nm, m/e 548 (M+1).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. custompartitioned between EtOAc and H2O
  3. customThe phases were separated
  4. extractionthe aqueous phase was re-extracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1

Sources & evidence

ORD record
ord-57a36a7fba3743c7b512522ee06a7fbe
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…