2-Fluorobenzylamine → HCID 59612373, compound

HRID 1890109Notes

Reaction equation

HRID 1890109 reaction equation
BrC1C2N(N=C(Cl)N=2)C=CC=1.FC1C=CC=CC=1CN.[Cl:21][C:22]1[N:39]=[C:25]2[C:26]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[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>>[Cl:21][C:22]1[N:39]=[C:25]2[C:26]([NH:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[CH:27][CH:28]=[CH:29][N:24]2[N:23]=1.[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][NH:30][C:26]1[C:25]2[N:24]([N:23]=[C:22]([NH:50][C:49]3[CH:51]=[CH:52][CH:53]=[C:47]([N:44]4[CH2:43][CH2:42][N:41]([CH3:40])[CH2:46][CH2:45]4)[CH:48]=3)[N:39]=2)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 666492-FluorobenzylamineHCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 67479005HCID 67479005, compoundHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 2

HCID 59612373HCID 59612373, compoundHCID 67479005HCID 67479005, compound

Procedure

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-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 2-fluorobenzylamine (1.11 mL, 9.72 mmol) in a manner analogous to Example 2d. Product isolated as an off-white solid, (1.45 g. 61%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.11 (d, J=6.9 Hz, 1H), 7.39-7.26 (m, 2H), 7.23-7.10 (m, 3H), 6.98 (t, J=14.0, 7.3 Hz, 1H), 6.43 (d, J=8.0 Hz, 1H), 4.53 (d, J=6.1 Hz, 2H). 395b) N(8)-(2-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)-(2-fluoro-benzyl)-amine (0.3227 g, 1.166 mmol) and 3-(4-methylpiperazin-1-yl)aniline (223 mg, 1.17 mmol) in a manner analogous to Example 2d. Product isolated as a red foam (102.96 mg, 20.5%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.19 (s, 1H), 7.98 (d, J=7.3 Hz, 1H), 7.43-7.06 (m, 7H), 6.74 (t, J=14.3, 7.1 Hz, 1H), 6.46 (d, J=8.6 Hz, 1H), 6.35 (m, 2H), 4.59 (d, J=6.4 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, (1.45 g. 61%)

Sources & evidence

ORD record
ord-b9f2f09e043a498a8a15886d50fb507c
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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