4-Pyridinemethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-4-ylmethyl)isonicotinamide

HRID 714379Notes

Reaction equation

HRID 714379 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][C:48]([CH2:51][NH2:52])=[CH:47][CH:46]=1>>[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:48]3[CH:49]=[CH:50][N:45]=[CH:46][CH:47]=3)=[O:17])[C:8]2=[O:22])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 773174-PyridinemethanamineHCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445532842-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-4-ylmethyl)isonicotinamideYield 60%

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-4-ylmethanamine, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-4-ylmethyl)isonicotinamide was obtained as a colorless solid in 60% yield: mp 160-162° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.7-8.52 (m, 3H), 8.37 (d, J=5.1 Hz, 1H), 7.39 (d, J=5.1 Hz, 1H), 7.31-7.15 (m, 3H), 4.60 (d, J=4.5 Hz, 2H), 4.06 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.13 (d, J=6.9 Hz, 2H), 0.99-0.91 (m, 1H), 0.60-0.49 (m, 2H), 0.29-0.15 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 156.9, 153.2, 149.8, 148.5, 147.3, 142.2, 122.5, 115.8, 108.8, 48.6, 42.8, 41.6, 41.5, 9.0, 3.4; MS (ES+) m/z 352.3 (M+1).

Sources & evidence

ORD record
ord-6a198ec4874b431ca0258356efad20b2
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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