Benzylamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)isonicotinamide

HRID 714370Notes

Reaction equation

C(N)C1C=CC=CC=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1.[F:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][N:37]=3)[C:31](OC)=[O:32])[C:24]2=[O:38])=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:35]=[CH:36][N:37]=3)[C:31]([NH:16][CH2:15][C:11]3[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=3)=[O:32])[C:24]2=[O:38])=[CH:39][CH:40]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 310183-Pyridinemethanamine

HCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445531052-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)isonicotinamideYield 39%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with pyridin-3-ylmethanamine to react with methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)isonicotinamide was obtained as a colorless solid in 39% yield: mp 153-155° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.29 (br, 1H), 8.60 (s, 1H), 8.52 (d, J=2.1 Hz, 1H), 8.44-8.42 (m, 1H), 8.37 (d, J=5.4 Hz, 1H), 7.71-7.68 (m, 1H), 7.35-7.31 (m, 4H), 7.18-7.13 (m, 2H), 4.46 (d, J=6.0 Hz, 2H), 4.39 (s, 2H), 3.93 (t, J=7.5 Hz, 2H), 3.38-3.34 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.8, 156.8, 153.5, 149.3, 148.7, 148.5, 143.2, 135.7, 135.1, 133.6, 133.6, 130.4, 130.3, 124.0, 116.0, 115.7, 115.2, 110.4, 46.6, 41.6, 41.2, 41.0; MS (ES+) m/z 406.2 (M+1).

Sources & evidence

ORD record: ord-02ef1b779b284b5fb3256c9e0467bbb5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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