Hydrochloric Acid → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-amine hydrochloric acid salt

HRID 472523Notes

Reaction equation

HRID 472523 reaction equation
[Cl:1][C:2]1[N:21]=[C:5]2[C:6]([O:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[N:22]1([CH2:27][CH2:28][N:29]2[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]2)[CH2:26][CH2:25][CH2:24][CH2:23]1.Cl>O1CCOCC1>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:34][C:32]4[CH:31]=[N:30][N:29]([CH2:28][CH2:27][N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH:33]=4)[N:21]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18].[ClH:1].[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:34][C:32]4[CH:31]=[N:30][N:29]([CH2:28][CH2:27][N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH:33]=4)[N:21]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 621376891-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-amineHCID 674813922-Chloro-8-(4-methanesulfonyl-phenoxy)-[1,2,4]triazolo[1,5-a]pyridine

Product 2

HCID 68775120[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-amine hydrochloric acid saltHCID 68775738[8-(4-Methanesulfonyl-phenoxy)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[8-(4-Methanesulfonyl-phenoxy)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-amine was synthesized from 2-chloro-8-(4-methanesulfonyl-phenoxy)-[1,2,4]triazolo[1,5-a]pyridine (0.100 g, 0.309 mmol) and 1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-ylamine (0.072 g, 0.402 mmol) in a manner analogous to Example 2d. The isolated pure product was treated with 2N hydrogen chloride in dioxane. [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-amine hydrochloric acid salt was isolated as a tan solid (81 mg, 56%). MP=Softened at 146-149° C. then melted at 215-217° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.55 (brs, 1H), 9.45 (s, 1H), 8.66 (d, J=6.26 Hz, 1H), 7.89 (d, J=8.13 Hz, 2H), 7.82 (s, 1H), 7.48 (s, 2H), 7.46 (s, 1H), 7.22 (d, J=8.23 Hz, 2H), 7.02 (t, J=6.93 Hz, 1H), 4.48 (brs, 2H), 4.18 (brs, 3H), 3.585 (d, J=4.90 Hz, 2H), 3.43 (brs, 2H), 2.92 (brs, 2H), 1.95 (brs, 2H), 1.82 (brs, 2H). MS=468 (MH)+.

Sources & evidence

ORD record
ord-0fafce17b36f4d66bc67808ef7e9c838
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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