3-Pyridinemethanamine → HCID 69317441, compound

HRID 2113570Notes

Reaction equation

HRID 2113570 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9](F)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.[NH2:27][CH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH2:28][NH:27][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][N:8]=2)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]3[NH:22][C:21]2[CH:23]=[CH:24][C:18]([O:17][C:16]([F:25])([F:26])[F:15])=[CH:19][CH:20]=2)[CH:30]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 6008484-(Trifluoromethoxy)anilineHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69317441HCID 69317441, compoundYield 3.8%

Procedure

Following the procedure described above in Example 29, 4-chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.200 g, 0.963 mmol) was reacted with 4-(trifluoromethoxy)aniline (0.14 mL, 0.19 g, 1.1 mmol), then with 3-(aminomethyl)pyridine. The crude product was purified twice by preparative HPLC, and lyophilized to give a fluffy, bright yellow solid (16 mg, 3.8% yield): 1H NMR (400 MHz, DMSO-D6) δ 4.57 (d, J=6.6 Hz, 2 H) 7.12 (s, 1 H) 7.33 (dd, J=7.6, 4.8 Hz, 1 H) 7.38 (s, 4 H) 7.52 (t, J=6.1 Hz, 1 H) 7.75 (d, J=7.6 Hz, 1 H) 8.29 (s, 1 H) 8.43 (d, J=3.8 Hz, 1 H) 8.59 (s, 1 H) 8.86 (s, 1 H) 9.67 (s, 1 H).

Workup

  1. customThe crude product was purified twice by preparative HPLC

Sources & evidence

ORD record
ord-03e8753499404fe9be7717fa26108d49
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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