3-Methoxybenzylamine → HCID 59612476, compound

HRID 1890104Notes

Reaction equation

HRID 1890104 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([Cl:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18].Cl[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]=3OC)=[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:11][C:9]1[N:10]=[C:3]2[C:2]([NH:18][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=3)=[CH:7][CH:6]=[CH:5][N:4]2[N:8]=1.[CH3:12][O:13][C:37]1[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH:31][C:27]1[C:26]2[N:25]([N:24]=[C:23]([NH:55][C:52]3[CH:53]=[CH:54][C:49]([N:46]4[CH2:45][CH2:44][N:43]([CH3:42])[CH2:48][CH2:47]4)=[CH:50][CH:51]=3)[N:41]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 211563-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

Product 2

HCID 59612476HCID 59612476, compoundHCID 67481427(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine

Procedure

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-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 3-methoxy-benzylamine (1.26 mL, 9.72 mmol) in a manner analogous to Example 2d. Product was isolated as an off-white solid, (1.90 g. 77%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.08 (d, J=6.4 Hz, 1H), 7.24 (m, 2H), 6.96 (s, 3H), 6.79 (d, J=8.0 Hz, 1H), 6.41 (d, J=8.0 Hz, 1H), 4.44 (d, J=5.9 Hz, 2H), 3.71 (s, 3H). 390b) N(8)-(3-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 was isolated as a red foam (36.85 mg, 24%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.03 (s, 1H), 7.92 (d, J=6.7 Hz, 1H), 7.57 (d, J=8.4 Hz, 2H), 7.23 (t, J=15.4, 8.1 Hz, 1H), 6.96 (s, 2H), 6.88 (d, J=8.1 Hz, 2H), 6.80 (d, J=8.6 Hz, 1H), 6.68 (t, J=14.6, 7.4 Hz, 1H), 6.40 (m, 1H), 6.29 (d, J=7.6 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H), 3.72 (s, 3H), 3.03 (s, 4H), 2.46 (s, 4H), 2.20 (s, 3H). MS=444 (MH)+.

Workup

  1. customProduct was isolated as an off-white solid, (1.90 g. 77%)

Sources & evidence

ORD record
ord-d2eee7b7d6be4b1e8109573dba5ad827
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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