3-Pyridinemethanamine → HCID 69316364, compound

HRID 2113569Notes

Reaction equation

HRID 2113569 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:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].[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:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:18]([O:17][C:16]([F:25])([F:26])[F:15])[CH:19]=2)[CH:30]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 737533-(Trifluoromethoxy)anilineHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69316364HCID 69316364, compoundYield 0.36%

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 3-(trifluoromethoxy)aniline (0.14 mL, 0.19 g, 1.1 mmol), then with 3-(aminomethyl)pyridine. The crude product was purified by preparative HPLC and lyophilized to give a fluffy, bright yellow solid (1.5 mg, 0.36% yield): 1H NMR (400 MHz, DMSO-D6) δ 4.56 (d, J=6.8 Hz, 2 H) 7.03-7.29 (m, 4 H) 7.33 (dd, J=8.0, 4.9 Hz, 1 H) 7.48 (br s, 2 H) 7.74 (d, J=7.3 Hz, 1 H) 8.31 (br s, 1 H) 8.43 (d, J=4.8 Hz, 1 H) 8.58 (s, 1 H) 8.87 (br s, 1 H) 9.73 (br s, 1 H).

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-17096dc48f9d42b5873927d789352449
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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