N-(2-(p-bromophenoxy)ethyl)pyrrolidine → N-Methyl-N-(3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-phenyl)-methanesulfonamide

HRID 472398Notes

Reaction equation

HRID 472398 reaction equation
[NH2:1][C:2]1[N:22]=[C:5]2[C:6]([C:10]3[CH:11]=[C:12]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Br[C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:21][N:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:1][C:24]4[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH2:30][N:31]5[CH2:32][CH2:33][CH2:34][CH2:35]5)=[CH:36][CH:37]=4)[N:22]=3)[CH:9]=[CH:8][CH:7]=2)[CH:11]=1)[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

4

Reactant 3

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67481389N-[3-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-phenyl]-N-methyl-methanesulfonamide

Product 1

HCID 67481471N-Methyl-N-(3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-phenyl)-methanesulfonamide

Procedure

N-Methyl-N-(3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-phenyl)-methanesulfonamide was prepared from N-[3-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-phenyl]-N-methyl-methanesulfonamide (75.0 mg, 0.236 mmol) and 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (71.0 mg, 0.263 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan foam (0.018 g, 15%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.31 (d, J=6.4 Hz, 1H), 8.13 (s, 3H), 7.93 (d, J=7.8 Hz, 1H), 7.60 (d, J=7.4 Hz, 1H), 7.56-7.46 (m, 3H), 7.46 (d, J=8.9 Hz, 1H), 6.98-6.90 (m, 3H), 6.68 (s, 1H), 4.11 (t, J=6.0 Hz, 2H), 3.41 (s, 3H), 2.96-2.88 (m, 5H), 2.64 (br s, 4H), 1.87-1.77 (m, 4H). MS=507 (MH)+.

Sources & evidence

ORD record
ord-2bf237d4c86543d3855814365eda0a72
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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