Benzylamine → N-benzyl-2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinamide

HRID 714381Notes

Reaction equation

HRID 714381 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.[CH:25]1([CH2:28][N:29]2[C:33](=[O:34])[N:32]([C:35]3[CH:36]=[C:37]([CH:42]=[CH:43][N:44]=3)[C:38]([O:40]C)=O)[CH:31]=[N:30]2)[CH2:27][CH2:26]1.C(N)C1C=CC=CC=1>>[CH2:6]([NH:7][C:38](=[O:40])[C:37]1[CH:42]=[CH:43][N:44]=[C:35]([N:32]2[C:33](=[O:34])[N:29]([CH2:28][CH:25]3[CH2:26][CH2:27]3)[N:30]=[CH:31]2)[CH:36]=1)[C:5]1[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247813methyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate

Product 1

HCID 44553286N-benzyl-2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinamideYield 38%

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 and with methyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate to react with benzylamine, N-benzyl-2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinamide was obtained as a colorless solid in 38% yield: mp 137-139° C.; 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.51 (d, J=5.1 Hz, 1H), 8.43 (s, 1H), 7.74-7.72 (m, 1H), 7.36-7.23 (m, 5H), 6.85 (br s, 1H), 4.62 (d, J=5.7 Hz, 2H), 3.69 (d, J=6.9 Hz, 2H), 1.29-1.16 (m, 1H), 0.59-0.53 (m, 2H), 0.40-0.35 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 164.5, 151.2, 149.3, 147.9, 144.6, 137.3, 132.2, 128.9, 128.1, 127.9, 120.7, 109.3, 50.2, 44.4, 10.2, 3.6; MS (ES+) m/z 350.3 (M+1).

Sources & evidence

ORD record
ord-d610b693403242be84933a060a2ea78d
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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