2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → N-Methyl-N-(4-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-phenyl)-methanesulfonamide
Reaction equation
[NH2:1][C:2]1[N:22]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Br[C:24]1[CH:25]=[C:26]([N:30]2[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:21][N:16]([C:13]1[CH:12]=[CH:11][C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:1][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([N:30]5[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]5)[CH:25]=4)[N:22]=3)[CH:9]=[CH:8][CH:7]=2)=[CH:15][CH:14]=1)[S:17]([CH3:20])(=[O:19])=[O:18]Participants
Reactant 3
Product 1
Procedure
N-Methyl-N-(4-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-phenyl)-methanesulfonamide was prepared from N-[4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-phenyl]-N-methyl-methanesulfonamide (75.0 mg, 0.236 mmol) and 1-(3-bromo-phenyl)-4-methyl-piperazine (70.0 mg, 0.274 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (26.0 mg, 0.0476 mmol) as the ligand in an analogous manner to Step 2d and was isolated as a tan solid (0.038 g, 33%). MP=202-204° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.43 (d, J=6.9 Hz, 1H), 8.06 (d, J=7.4 Hz, 2H), 7.58 (d, J=7.1 Hz, 1H), 7.52 (d, J=7.4 Hz, 2H), 7.36 (s, 1H), 7.25-7.19 (m, 1H), 7.00-6.95 (m, 2H), 6.83 (s, 1H), 6.59 (d, J=8.4 Hz, 1H), 3.39 (s, 3H), 3.30-3.25 (m, 4H), 2.90 (s, 3H), 2.63-2.58 (m, 4H), 2.37 (s, 3H). MS=492 (MH)+.
Sources & evidence
- ORD record
- ord-23f175fdbd2346ccb31ec7d8a813b95b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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