4-Fluorobenzylamine → 4-Fluorobenzylamine

HRID 1890110Notes

Reaction equation

HRID 1890110 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.Cl[C:22]1[N:39]=[C:25]2[C:26]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][CH:28]=[CH:29][N:24]2[N:23]=1.[CH3:40][N:41]1[CH2:46][CH2:45][N:44]([C:47]2[CH:48]=[C:49]([CH:51]=[CH:52][CH:53]=2)[NH2:50])[CH2:43][CH2:42]1>>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.[F:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][NH:30][C:26]2[C:25]3[N:24]([N:23]=[C:22]([NH:50][C:49]4[CH:51]=[CH:52][CH:53]=[C:47]([N:44]5[CH2:43][CH2:42][N:41]([CH3:40])[CH2:46][CH2:45]5)[CH:48]=4)[N:39]=3)[CH:29]=[CH:28][CH:27]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 673264-FluorobenzylamineHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridineHCID 67481441(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(4-fluoro-benzyl)-amine

Product 2

HCID 673264-FluorobenzylamineHCID 59612491N(8)-(4-Fluoro-benzyl)-N(2)-[3-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(4-fluoro-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-fluorobenzylamine (1.11 mL, 9.72 mmol) in a manner analogous to Example 2d. Product isolated as an off-white solid, (1.94 g. 82%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.08 (d, J=6.5 Hz, 1H), 7.42 (m, 2H), 7.29 (m, 1H), 7.13 (t, J=17.1, 8.6 Hz, 2H), 6.95 (t, J=14.7, 7.3 Hz, 1H), 6.42 (d, J=7.8 Hz, 1H), 4.45 (d, J=6.0 Hz, 2H). 396b) N(8)-(4-Fluoro-benzyl)-N(2)-[3-(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)-(4-fluoro-benzyl)-amine (0.288 g, 1.04 mol) and 3-(4-methylpiperazin-1-yl)aniline (223 mg, 1.17 mol) in a manner analogous to Example 2d. Product isolated as red foam (83.06 mg, 18.5%). 1H NMR (400 MHz, (D3C)2SO, δ, pap): 9.16 (s, 1H), 7.96 (d, J=6.3 Hz, 1H), 7.43 (t, J=12.8, 6.7 Hz, 2H), 7.26 (m, 2H), 7.18-7.06 (m, 3H), 6.72 (t, J=14.3, 7.2 Hz, 1H), 6.45 (m, 2H), 6.32 (d, J=8.4 Hz, 1H), 4.50 (d, J=5.7 Hz, 2H), 3.11 (s, 4H), 2.45 (s, 4H), 2.22 (s, 3H). MS=432 (MH)+.

Workup

  1. customProduct isolated as an off-white solid, (1.94 g. 82%)

Sources & evidence

ORD record
ord-9f15c39c6a7d4454b8e2fae5c057f0cf
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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