4-(2-(Pyrrolidin-1-yl)ethoxy)aniline → N-Methyl-N-[2-({2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-methyl)-phenyl]-methanesulfonamide
Reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[N:25]1([CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:23][N:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:39][C:36]3[CH:37]=[CH:38][C:33]([O:32][CH2:31][CH2:30][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:34][CH:35]=3)[N:24]=2)[CH:9]=[CH:8][CH:7]=1)[S:19]([CH3:22])(=[O:21])=[O:20]Participants
Reactant 3
Product 1
Procedure
N-Methyl-N-[2-({2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-methyl)-phenyl]-methanesulfonamide was prepared from N-{2-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-phenyl}-N-methyl-methanesulfonamide (75.0 mg, 0.205 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (48.0 mg, 0.233 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (23.0 mg, 0.0421 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.026 g, 24%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.79 (d, J=6.7 Hz, 1H), 7.55-7.45 (m, 3H), 7.38-7.28 (m, 3H), 6.92 (d, J=8.9 Hz, 2H), 6.65 (t, J=7.5 Hz, 1H), 6.51 (s, 1H), 6.36 (d, J=7.7 Hz, 1H), 5.21 (t, J=5.7 Hz, 1H), 4.72 (d, J=6.1 Hz, 2H), 4.10 (t, J=6.0 Hz, 2H), 3.31 (s, 3H), 3.00 (s, 3H), 2.90 (t, J=5.9 Hz, 2H), 2.66-2.59 (m, 4H), 1.85-1.77 (m, 4H). MS=536 (MH)+.
Sources & evidence
- ORD record
- ord-88199de39ec9462e955df1127b8f8b20
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501936B2
Reaction notes
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