4-Methoxybenzylamine → HCID 59612442, compound

HRID 1890105Notes

Reaction equation

HRID 1890105 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.COC1C=CC(CN)=CC=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.[Cl:36][C:37]1[N:55]=[C:40]2[C:41]([NH:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)=[CH:42][CH:43]=[CH:44][N:39]2[N:38]=1>>[Cl:36][C:37]1[N:55]=[C:40]2[C:41]([NH:45][CH2:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)=[CH:42][CH:43]=[CH:44][N:39]2[N:38]=1.[CH3:54][O:53][C:50]1[CH:49]=[CH:48][C:47]([CH2:46][NH:45][C:41]2[C:40]3[N:39]([N:38]=[C:37]([NH:35][C:32]4[CH:33]=[CH:34][C:29]([N:26]5[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]5)=[CH:30][CH:31]=4)[N:55]=3)[CH:44]=[CH:43][CH:42]=2)=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 754524-MethoxybenzylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridineHCID 67481371HCID 67481371, compound

Product 2

HCID 59612442HCID 59612442, compoundHCID 67481371HCID 67481371, compound

Procedure

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(4-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 4-methoxy-benzenemethanamine, (1.26 mL, 9.72 mmol) in a manner analogous to Example 2d. Product isolated as an off-white solid, (1.51 g. 61%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.06 (d, J=6.90 Hz, 1H), 7.31 (d, J=8.2 Hz, 2H), 7.19 (m, 1H), 6.94 (t, J=14.4, 7.6 Hz, 1H), 6.87 (d, J=7.4 Hz, 2H), 6.42 (d, J=8.0 Hz, 1H), 4.40 (d, J=6.1 Hz, 2H), 3.71 (s, 3H). MS=289 (MH)+. 391b) N(8)-(4-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 4-(4-methyl-piperazin-1-yl)-phenylamine (74.2 mg, 0.388 mmol) and (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(4-methoxy-benzyl)-amine (99.9 mg, 0.346 mmol) in a manner analogous to Example 2d. Product was isolated as a red foam (10.64 mg, 7%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.03 (s, 1H), 7.92 (d, J=6.2 Hz, 1H), 7.56 (d, J=8.3 Hz, 2H), 7.32 (d, J=7.8 Hz, 2H), 6.88 (d, J=8.3 Hz, 4H), 6.68 (t, J=13.9, 7.0 Hz, 1H), 6.29 (m, 2H), 4.42 (m, 2H), 3.72 (s, 3H), 3.03 (s, 4H), 2.47 (s, 4H), 2.22 (s, 3H). MS=444 (MH)+.

Workup

  1. customProduct isolated as an off-white solid, (1.51 g. 61%)

Sources & evidence

ORD record
ord-fd3975659f9b4e66b0472736b56aa7f2
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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