2-Pyridinemethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-2-ylmethyl)isonicotinamide

HRID 714378Notes

Reaction equation

HRID 714378 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.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH2:51][NH2:52]>>[CH:5]1([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]([NH:52][CH2:51][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=3)=[O:17])[C:8]2=[O:22])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 195092-PyridinemethanamineHCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445532832-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-2-ylmethyl)isonicotinamideYield 71%

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 pyridin-2-ylmethanamine, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-2-ylmethyl)isonicotinamide was obtained as a colorless solid in 71% yield: mp 122-123° C.; 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 8.53 (d, J=5.1 Hz, 1H), 8.34 (d, J=5.1 Hz, 1H), 7.77-7.63 (m, 2H), 7.43-7.34 (m, 2H), 7.23-7.18 (m, 1H), 4.74 (d, J=5.1 Hz, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.16 (d, J=7.2 Hz, 2H), 1.00-0.87 (m, 1H), 0.57-0.50 (m, 2H), 0.25-0.20 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 166.1, 156.9, 155.7, 153.3, 148.4, 148.2, 142.9, 137.6, 122.7, 122.6, 115.5, 109.5, 48.6, 44.5, 41.6, 41.5, 9.1, 3.4; MS (ES+) m/z 352.3 (M+1).

Sources & evidence

ORD record
ord-013acaa353c543b69628784e1f49ae01
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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