2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → 1-(3-{8-[4-(Dimethyl-phosphinoyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-phenyl)-4-ethyl-piperazin-2-one
Reaction equation
Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([P:16]([CH3:19])([CH3:18])=[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][CH3:35])[CH2:30][C:29]2=[O:36])[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:18][P:16]([CH3:19])([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[CH2:33][CH2:32][N:31]([CH2:34][CH3:35])[CH2:30][C:29]5=[O:36])[CH:25]=[CH:26][CH:27]=4)[N:20]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:11][CH:12]=1)=[O:17]Participants
Reactant 3
Product 1
Procedure
1-(3-{8-[4-(Dimethyl-phosphinoyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-phenyl)-4-ethyl-piperazin-2-one was prepared from 2-chloro-8-[4-(dimethyl-phosphinoyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine (100.0 mg, 0.3271 mmol) and 1-(3-amino-phenyl)-4-ethyl-piperazin-2-one (79.0 mg, 0.360 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (28.0 mg, 0.0512 mmol) as the ligand in a manner analogous to Example 2d. MP=205-207° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.48 (d, J=6.6 Hz, 1H), 8.13 (d, J=7.9 Hz, 2H), 7.92-7.85 (m, 2H), 7.68 (s, 1H), 7.63 (d, J=7.2 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 7.04-6.97 (m, 2H), 6.93 (d, J=7.5 Hz, 1H), 3.80-3.75 (m, 2H), 3.35 (s, 2H), 2.88-2.83 (m, 2H), 2.57 (q, J=7.0 Hz, 2H), 1.80 (s, 3H), 1.77 (s, 3H), 1.18 (t, J=7.0 Hz, 3H). MS=489 (MH)+.
Sources & evidence
- ORD record
- ord-385edb7b80534ca8bda844b9055bfd04
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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