4-(1-Methylpiperidin-4-yl)aniline → N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[4-(1-methyl-piperidin-4-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472414ノート

反応式

HRID 472414 の反応式
Cl[C:2]1[N:22]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:21][S: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:36][C:33]3[CH:34]=[CH:35][C:30]([CH:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)=[CH:31][CH:32]=3)[N:22]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:20])=[O:19]

参加物

4

反応物 3

HCID 219595294-(1-Methylpiperidin-4-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479011(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonyl-benzyl)-amine

生成物 1

HCID 49839375N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[4-(1-methyl-piperidin-4-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

実験手順

N(8)-(2-Methanesulfonyl-benzyl)-N(2)-[4-(1-methyl-piperidin-4-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methanesulfonyl-benzyl)-amine (75.0 mg, 0.223 mmol) and 4-(1-methyl-piperidin-4-yl)-phenylamine (47.0 mg, 0.247 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 (0.042 g, 38%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.11 (d, J=8.2 Hz. 1H), 7.85 (d, J=6.7 Hz, 1H), 7.67-7.59 (m, 2H), 7.55-7.46 (m, 3H), 7.20 (d, J=8.5 Hz, 2H), 6.69 (t, J=7.4 Hz, 1H), 6.37 (s, 1H), 6.42 (d, J=7.6 Hz, 1H), 5.29 (t, J=6.1 Hz, 1H), 4.96 (d, J=6.1 Hz, 2H), 3.16 (s, 3H), 3.01-2.94 (m, 2H), 2.50-2.39 (m, 1H), 2.33 (s, 3H), 2.10-2.00 (m, 2H), 1.86-1.73 (m, 4H). MS=491 (MH)+.

出典と根拠

ORDレコード
ord-5049dc2010b841f098dcb8069d2929e4
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

反応ノート

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