Hydrochloric Acid → HCID 178481757, compound

HRID 2204661Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[CH3:13][NH:14][NH2:15].Cl.O>CCCCO>[CH3:13][N:14]1[C:2]2=[C:3]3[CH:12]=[CH:11][NH:10][C:4]3=[N:5][CH:6]=[C:7]2[CH:8]=[N:15]1

Participants

Conditions

Temperature: 120 °C

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.37 g, 7.59 mmol, Adesis) and methylhydrazine (0.599 mL, 11.4 mmol) in n-BuOH (7 mL) were heated to about 95° C. After about 15 min, concentrated HCl (0.500 mL, 16.4 mmol) was added and the reaction mixture was heated to about 120° C. After about 4 h, water (10 mL) was added and the mixture was extracted with EtOAc (20 mL). The organic layer was separated and the aqueous layer was basified with saturated aqueous NaHCO3 to about pH 8 and extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (40 g column) eluting with a gradient of 5-60% EtOAc in heptane to give 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.960 g, 74%): LC/MS (Table 2, Method d) Rt=1.40 min; MS m/z: 173 (M+H)+.

Workup

waitAfter about 4 h
extractionthe mixture was extracted with EtOAc (20 mL)
customThe organic layer was separated
extractionextracted with EtOAc (2×20 mL)
dry with materialThe combined organic layers were dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (40 g column)
washeluting with a gradient of 5-60% EtOAc in heptane

Sources & evidence

ORD record: ord-f2fa7acef84143e193428067b0d74ec8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365579B2

Reaction notes

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