Benzylamine → N-benzyl-2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinamide

HRID 714376Notes

Reaction equation

HRID 714376 reaction equation
FC1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=3)[C:15]([O:17]C)=O)[C:8]2=[O:22])=CC=1.C1(CN2CCN(C3C=C(C=CN=3)C(OC)=O)C2=O)CC1.[CH2:45]([NH2:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[CH2:45]([NH:52][C:15](=[O:17])[C:14]1[CH:19]=[CH:20][N:21]=[C:12]([N:9]2[CH2:10][CH2:11][N:7]([CH2:6][CH:5]3[CH2:23][CH2:24]3)[C:8]2=[O:22])[CH:13]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44553281N-benzyl-2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinamideYield 31%

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-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate to react with benzylamine, N-benzyl-2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 31% yield: mp 121-123° C.; 1H NMR (300 MHz, CDCl3) δ 8.54 (s, 1H), 8.36 (d, J=5.4 Hz, 1H), 7.40 (d, J=5.1 Hz, 1H), 7.32-7.24 (m, 5H), 6.73 (br s, 1H), 4.60 (d, J=6.0 Hz, 2H), 4.06 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.14 (d, J=6.9 Hz, 2H), 1.00-0.87 (m, 1H), 0.57-0.51 (m, 2H), 0.24-0.19 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 156.9, 153.2, 148.2, 142.9, 137.7, 128.8, 128.0, 127.7, 115.9, 108.8, 48.6, 44.2, 41.6, 41.5, 31.0, 9.0, 3.4; MS (ES+) m/z 351.3 (M+1).

Sources & evidence

ORD record
ord-c18d7c15f3554a9c8500bf71beb82d3f
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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