4-(1-Methylpiperidin-4-yl)aniline → HCID 59612530, compound

HRID 1889911Notes

Reaction equation

HRID 1889911 reaction equation
Cl[C:2]1[N:22]=[C:5]2[C:6]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:21][S:18]([CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:36][C:33]3[CH:34]=[CH:35][C:30]([CH:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)=[CH:31][CH:32]=3)[N:22]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:20])=[O:19]

Participants

4

Reactant 3

HCID 219595294-(1-Methylpiperidin-4-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479152HCID 67479152, compound

Product 1

HCID 59612530HCID 59612530, compound

Procedure

N(8)-(2-Methanesulfonylmethyl-phenyl)-N(2)-[4-(1-methyl-piperidin-4-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonylmethyl-phenyl)-amine (75.0 mg, 0.223 mmol) and 4-(1-methyl-piperidin-4-yl)-phenylamine (47.0 mg, 0.247 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.016 g, 15%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.97 (d, J=6.6 Hz, 1H), 7.74 (s, 1H), 7.59-7.52 (m, 3H), 7.44-7.37 (m, 2H), 7.23-7.15 (m, 3H), 6.87-6.84 (m, 2H), 6.69 (t, J=7.3 Hz, 1H), 4.45 (s, 2H), 3.01-2.93 (m, 5H), 2.50-2.40 (m, 1H), 2.32 (s, 3H), 2.09-2.01 (m, 2H), 1.87-1.74 (m, 4H). MS=491 (MH)+.

Sources & evidence

ORD record
ord-5f9709b1cd1b497c9016f468ff9d1e14
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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