Benzylamine → N-benzyl-2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinamide

HRID 714387Notes

Reaction equation

HRID 714387 reaction equation
F[C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2CCN(C3C=C(C=CN=3)C(OC)=O)C2=O)=[CH:4][CH:3]=1.[O:25]=[C:26]1[N:30]([CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH2:29][CH2:28][N:27]1[C:38]1[CH:39]=[C:40]([CH:45]=[CH:46][N:47]=1)[C:41]([O:43]C)=O.C(N)C1C=CC=CC=1>>[CH2:6]([NH:7][C:41](=[O:43])[C:40]1[CH:45]=[CH:46][N:47]=[C:38]([N:27]2[CH2:28][CH2:29][N:30]([CH2:31][C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)[C:26]2=[O:25])[CH:39]=1)[C:5]1[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 58247761Methyl 2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44553453N-benzyl-2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinamideYield 37%

Procedure

Following the procedure as described in Example 15, making variations as required to replace methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate with methyl 2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinate to react with benzylamine, N-benzyl-2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 37% yield: mp 154-156° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.25 (t, J=5.9 Hz, 1H), 8.60 (s, 1H), 8.52-8.50 (m, 2H), 8.38 (d, J=5.4 Hz, 1H), 7.37-7.18 (m, 8H), 4.45-4.43 (m, 4H), 3.99 (t, J=7.9 Hz, 2H), 3.42 (t, J=7.9 Hz, 2H); MS (ES+) m/z 387.8 (M+1).

Sources & evidence

ORD record
ord-55f7261f7354492e931687984e6c52d8
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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