HCID 22330138, compound → HCID 49838646, compound

HRID 1889899Notes

Reaction equation

HRID 1889899 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.[NH2:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][OH:36])[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[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:21][C:22]4[CH:23]=[C:24]([N:28]5[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][OH:36])[CH2:32][CH2:33]5)[CH:25]=[CH:26][CH:27]=4)[N:20]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 22330138HCID 22330138, compoundHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674814372-Chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 49838646HCID 49838646, compound

Procedure

2-(4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanol was prepared from 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (75.0 mg, 0.244 mmol) and 2-[4-(3-amino-phenyl)-piperazin-1-yl]-ethanol (60.0 mg, 0.271 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 (0.052 g, 43%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.49 (d, J=6.5 Hz, 1H), 8.26 (d, J=8.4 Hz, 2H), 8.08 (d, J=8.4 Hz, 2H), 7.66 (d, J=7.5 Hz, 1H), 7.45 (s, 1H), 7.23 (t, J=8.0 Hz, 1H), 7.02 (t, J=7.1 Hz, 1H), 6.96-6.92 (m, 1H), 6.87 (s, 1H), 6.62-6.58 (m, 1H), 3.70 (t, J=5.3 Hz, 2H), 3.30-3.26 (m, 4H), 3.11 (s, 3H), 3.74-2.70 (m, 4H), 2.64 (t, J=5.3 Hz, 2H). MS=493 (MH)+.

Sources & evidence

ORD record
ord-f7aca7639b5f4932b2947d907be84a3d
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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