2-Methoxybenzylamine → [1,2,4]Triazolo[1,5-a]pyridine-2,8-diamine, N8-[(2-methoxyphenyl)methyl]-N2-[4-(4-methyl-1-piperazinyl)phenyl]-

HRID 472643

反応式

HRID 472643 の反応式
BrC1C2N(N=C(Cl)N=2)C=CC=1.COC1C=CC=CC=1CN.[Cl:22][C:23]1[N:41]=[C:26]2[C:27]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1.[CH3:42][N:43]1[CH2:48][CH2:47][N:46]([C:49]2[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH2:45][CH2:44]1>>[Cl:22][C:23]1[N:41]=[C:26]2[C:27]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[CH:28][CH:29]=[CH:30][N:25]2[N:24]=1.[CH3:40][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][C:27]1[C:26]2[N:25]([N:24]=[C:23]([NH:55][C:52]3[CH:51]=[CH:50][C:49]([N:46]4[CH2:45][CH2:44][N:43]([CH3:42])[CH2:48][CH2:47]4)=[CH:54][CH:53]=3)[N:41]=2)[CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 812922-MethoxybenzylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 67479414(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amineHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

生成物 2

HCID 59612401[1,2,4]Triazolo[1,5-a]pyridine-2,8-diamine, N8-[(2-methoxyphenyl)methyl]-N2-[4-(4-methyl-1-piperazinyl)phenyl]-HCID 67479414(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine

実験手順

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (2.00 g, 8.60 mmol) and 2-methoxy-benzylamine in a manner analogous to Example 2d. Product isolated as a tan oil that solidified upon standing (1.56 g. 63%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.09 (d, J=6.7 Hz, 1H), 7.21 (m, 2H), 7.04-6.93 (m, 3H), 6.86 (t, J=14.5, 7.2 Hz, 1H), 6.35 (d, J=7.9 Hz, 1H), 4.43 (d, J=6.30 Hz, 2H), 3.86 (s, 3H). 387b) N(8)-(2-Methoxy-benzyl)-N(2)-[4-(4-methyl-piperazin-1-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-methoxy-benzyl)-amine (100.00 mg, 0.34634 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (74.2 mg, 0.388 mmol) in a manner analogous to Example 2d. Product isolated as a brown foam (23.79 mg, 15.5%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.07 (s, 1H), 7.93 (d, J=6.2 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.24 (m, 2H), 7.02 (d, J=8.4 Hz, 1H), 6.88 (m, 3H), 6.70 (t, J=13.70, 6.9 Hz, 1H), 6.29 (d, J=7.9 Hz, 1H), 6.09 (m, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.87 (s, 3H), 3.02 (s, 4H), 2.45 (s, 4H), 2.22 (s, 3H). MS=444 (MH)+.

後処理

  1. customProduct isolated as a tan oil that

出典と根拠

ORDレコード
ord-41f7947f4fe6478686e0b7c1f1427904
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

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