Methylhydrazine → HCID 178503130, compound

HRID 1628099Notes

Reaction equation

HRID 1628099 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=O)=[CH:6][N:5]=[C:4]2[NH:18][CH:19]=[CH:20][C:3]=12.[CH3:21][NH:22][NH2:23]>C(O)CCC>[CH3:21][N:22]1[C:2]2=[C:3]3[CH:20]=[CH:19][NH:18][C:4]3=[N:5][CH:6]=[C:7]2[C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[N:23]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58382173HCID 58382173, compound

Product 1

HCID 178503130HCID 178503130, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
95 °C

Procedure

To (4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)(4-(methylthio)phenyl)methanone (0.20 g, 0.66 mmol, prepared using S from 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde [Preparation #1, Step B] and AV) in BuOH (4 mL) was added methylhydrazine (0.052 mL, 0.991 mmol). The mixture was stirred for about 1.5 h at about 95° C. and then cooled to rt. The resulting precipitate was collected by filtration, washed with EtOAc (2 mL) and dried in a vacuum oven at about 70° C. for about 2 h to give 1-methyl-3-(4-(methylthio)phenyl)-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.15 g, 77%): LC/MS (Table 2, Method a) Rt=2.23 min.; MS m/z: 295 (M+H)+. Syk IC50=A.

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with EtOAc (2 mL)
  4. customdried in a vacuum oven at about 70° C. for about 2 h

Sources & evidence

ORD record
ord-ac10cd9289bd4f87980fda5dd27cbd43
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…