2-Methoxyethylamine → HCID 131715166, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[CH3:12][O:13][CH2:14][CH2:15][NH2:16]>>[CH3:12][O:13][CH2:14][CH2:15][NH:16][N:11]1[C:3]2[C:4](=[N:5][C:6]([CH3:8])=[CH:7][CH:2]=2)[CH:9]=[N:10]1Participants
Procedure
7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (D4) (1 g, 0.06 mole) was heated at reflux under nitrogen in methoxyethylamine for 1 week. Volatile material was removed under vacuum and the residue treated with water (15 ml) and a little methanol. A small amount of insoluble material was filtered off and the filtrate reevaporated to dryness. Chromatography on basic alumina eluting with ethyl acetate with methanol added to a maximum of 15% gave white gum. This was further purified by passing through Dowex 50W column, previously treated with dilute HCl, eluting initially with methanol, then water and finally 5% 0.880 ammonia in water. The fractions containing UV active material were freeze dried giving the title compound as a white solid (0.38 g,31%) m.p. 167°-170° (Found: C, 57.18; H, 6.84; N, 27.06 C10H14N4O.O.2H2O requires C,57.23; H, 6.90; N, 26.70%), δ(DMSOd-6) 2.4 (3H,s), 3.2-3.7 (4H,m), 6.25 (1H,s), 6.35 (1H,br.s), 7.9 (1H,s).
Workup
- customVolatile material was removed under vacuum
- additionthe residue treated with water (15 ml)
- filtrationA small amount of insoluble material was filtered off
- customthe filtrate reevaporated to dryness
- additionChromatography on basic alumina eluting with ethyl acetate with methanol added to a maximum of 15%
- customgave white gum
- customThis was further purified
- additionpreviously treated with dilute HCl
- washeluting initially with methanol
- additionThe fractions containing UV active material
- customdried
Sources & evidence
- ORD record
- ord-4ab8250602fa4fb2b2764f90011364ea
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04670432
Reaction notes
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