Methyl 4-aminobenzoate → HCID 69185151, compound

HRID 2113568Notes

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].[NH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.[NH2:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>>[C:13]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)=[CH:10][C:9]([NH:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[N:8][CH:7]=2)#[N:14]

Participants

Reactant 3

HCID 12082Methyl 4-aminobenzoate

HCID 310183-Pyridinemethanamine

HCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69185151HCID 69185151, compoundYield 2.5%

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 methyl 4-aminobenzoate (0.16 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 (9.7 mg, 2.5% yield): 1H NMR (400 MHz, DMSO-D6) δ 3.86 (none, 1 H) 4.55 (d, J=6.1 Hz, 2 H) 7.03 (s, 1 H) 7.20 (d, J=8.1 Hz, 2 H) 7.31 (dd, J=7.6, 5.1 Hz, 1 H) 7.48-7.61 (m, 1 H) 7.71 (d, J=8.1 Hz, 1 H) 7.91 (d, J=8.3 Hz, 2 H) 8.35-8.46 (m, 2 H) 8.56 (s, 1 H) 8.89 (s, 1 H).

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-2ef393d5670b49e7a3917c8ffaf75d02
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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