4-(1-Ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochloride → N-[4-(1-ethyl-4-oxido-1,4-azaphosphinan-4-yl)phenyl]-8-[4-(methylsulfonyl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 472670Notes

Reaction equation

HRID 472670 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.Cl.[CH2:22]([N:24]1[CH2:29][CH2:28][P:27]([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)(=[O:30])[CH2:26][CH2:25]1)[CH3:23]>>[CH2:22]([N:24]1[CH2:25][CH2:26][P:27]([C:31]2[CH:37]=[CH:36][C:34]([NH:35][C:2]3[N:20]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:33][CH:32]=2)(=[O:30])[CH2:28][CH2:29]1)[CH3:23]

Participants

3

Reactant 2

HCID 674788444-(1-Ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochlorideHCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 49839837N-[4-(1-ethyl-4-oxido-1,4-azaphosphinan-4-yl)phenyl]-8-[4-(methylsulfonyl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

N-[4-(1-ethyl-4-oxido-1,4-azaphosphinan-4-yl)phenyl]-8-[4-(methylsulfonyl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from 2-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (133 mg, 0.434 mmol) and 4-(1-ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochloride (131.01 mg, 0.47689 mmol) in a manner analogous to Example 2d. Product isolated as an off-white solid (31.56 mg, 14%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.54 (d, J=8.3 Hz, 1H), 8.23 (d, J=8.0 Hz, 2H), 8.01 (d, J=8.0 Hz, 2H), 7.80-7.67 (m, 5H), 7.08 (t, J=13.6, 7.0 Hz, 1H), 3.13-2.90 (m, 7H), 2.61 (m, 2H), 2.27-2.02 (m, 4H), 1.13 (t, J=13.6, 6.4 Hz, 3H). MS=510 (MH)+.

Sources & evidence

ORD record
ord-4af2cb804aa44dad9f0477fb9a0f5a30
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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