4-(2-(Pyrrolidin-1-yl)ethoxy)aniline → N(8)-Pyridin-3-ylmethyl-N(2)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 1889901Notes

Reaction equation

HRID 1889901 reaction equation
Cl[C:2]1[N:18]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][NH:10][C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:33][C:30]4[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:19]5[CH2:23][CH2:22][CH2:21][CH2:20]5)=[CH:28][CH:29]=4)[N:18]=3)[CH:9]=[CH:8][CH:7]=2)[CH:13]=1

Participants

4

Reactant 3

HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67481455(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-pyridin-3-ylmethyl-amine

Product 1

HCID 59612555N(8)-Pyridin-3-ylmethyl-N(2)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-Pyridin-3-ylmethyl-N(2)-[4-(2-pyrrolidin-1-yl-ethoxy)-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)-pyridin-3-ylmethyl-amine (75.0 mg, 0.289 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (67.0 mg, 0.325 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (33.0 mg, 0.0604 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.031 g, 25%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.67 (s, 1H), 8.56 (d, J=4.2 Hz, 1H), 7.83 (d, J=6.6 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.47 (d, J=8.8 Hz, 2H), 7.31-7.25 (m, 1H), 6.92 (d, J=8.8 Hz, 2H), 6.66 (t, J=7.1 Hz, 1H), 6.56 (s, 1H), 6.31 (d, J=7.6 Hz, 1H), 5.18 (t, J=5.4 Hz, 1H), 4.51 (d, J=5.6 Hz, 2H), 4.10 (t, J=6.0 Hz, 2H), 2.89 (t, J=5.9 Hz, 2H), 2.66-2.59 (m, 4H), 1.85-1.77 (m, 4H). MS=430 (MH)+.

Sources & evidence

ORD record
ord-38bbc9e5491945ed9de7f8a1d7800d47
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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