Methylamine → 2-(4-fluorophenyl)-N-methyl-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1373831Notes

Reaction equation

HRID 1373831 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:24][NH2:25]>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:25][CH3:24])[N:7]3[N:8]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 98584077-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 99667582-(4-fluorophenyl)-N-methyl-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-7-amineYield 77.3%

Procedure

7-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (25 mg, 0.077 mmol) and excess of methylamine in alcohol (1 mL) in sealed tube was heated at 120° C. for overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give 2-(4-fluorophenyl)-N-methyl-3-(4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine a peach solid in 77.3% yield. 1H NMR (CDCl3): δ 8.59 (d, 2H, J=5.4 Hz), 7.58–7.62 (m, 2H), 7.28–7.30 (m, 3H), 7.07–7.14 (m, 3H), 6.11 (bs, 1H), 6.00 (d, 1H, J=7.4 Hz), 3.16 (d, 3H, J=5.0 Hz); MS (ES+ve): 320 (18, M+2), 319 (20, M+1), 318 (100, M+).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-0b1dce21bad8403da6d728f62d955cf9
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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