2-Pyridinemethanamine → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-pyridin-2-ylmethyl-amine

HRID 472665Notes

Reaction equation

Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28]>>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:28][CH2:27][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)[N:20]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

Reactant 2

HCID 195092-Pyridinemethanamine

HCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 59612469[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-pyridin-2-ylmethyl-amine

Procedure

[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-pyridin-2-ylmethyl-amine was prepared from 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (250 mg, 0.81 mmol) and C-pyridin-2-yl-methylamine (0.84 mL, 8.1 mmol) in a manner analogous to Example 406. Product isolated as a light yellow powder (207 mg, 67%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.68 (d, J=6.5 Hz, 1H), 8.51 (m, 1H), 8.38 (d, J=7.7 Hz, 2H), 8.04 (d, J=7.9 Hz, 2H), 7.87 (d, J=7.7 Hz, 1H), 7.73 (t, J=15.5, 7.9 Hz, 1H), 7.46-7.37 (m, 2H), 7.24 (m, 1H), 7.04 (t, J=14.2, 6.9 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 3.28 (s, 3H). MS=380 (MH)+.

Sources & evidence

ORD record: ord-2fa43979a3ca4ff39e24bc1a39aeadd0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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