2-(4-(4-Aminophenyl)piperazin-1-yl)ethan-1-ol → N-{3-[(2-{4-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-phenylamino}-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide

HRID 1889902

Reaction equation

HRID 1889902 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][OH:40])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[OH:40][CH2:39][CH2:38][N:35]1[CH2:34][CH2:33][N:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:2]3[N:24]=[C:5]4[C:6]([NH:10][CH2:11][C:12]5[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=5)=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:27][CH:28]=2)[CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 7671002-(4-(4-Aminophenyl)piperazin-1-yl)ethan-1-olHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67478948N-{3-[(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide

Product 1

HCID 49838898N-{3-[(2-{4-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-phenylamino}-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide

Procedure

N-{3-[(2-{4-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-phenylamino}-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide was prepared from N-{3-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulfonamide (75.0 mg, 0.204 mmol) and 2-[4-(4-amino-phenyl)-piperazin-1-yl]-ethanol (50.0 mg, 0.226 mmol) with 2,2′-Bis-dicyclohexylphosphanyl-biphenyl (26.0 mg, 0.0476 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.052 g, 46%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.41 (d, J=4.5 Hz, 1H), 7.85 (d, J=7.2 Hz, 1H), 7.81 (d, J=6.7 Hz, 1H), 7.48 (d, J=8.8 Hz, 2H), 7.30-7.25 (m, 1H), 6.96 (d, J=8.8 Hz, 2H), 6.64 (t, J=7.3 Hz, 1H), 6.56 (s, 1H), 6.29 (d, J=7.7 Hz, 1H), 5.33-5.28 (m, 1H), 4.17 (d, J=6.1 Hz, 2H), 3.67 (t, J=5.3 Hz, 2H), 3.32 (s, 3H), 3.18-3.13 (m, 4H), 3.09 (s, 3H), 2.72-2.67 (m, 4H), 2.62 (t, J=5.4 Hz, 2H). MS=552 (MH)+.

Sources & evidence

ORD record
ord-7225a351476240fb91f93f351001c443
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Linked notes

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