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

HRID 714377Notes

Reaction equation

HRID 714377 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]=[C:47]([CH2:51][NH2:52])[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:47]3[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=3)=[O:17])[C:8]2=[O:22])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445532822-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)isonicotinamideYield 46%

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-3-ylmethanamine, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)isonicotinamide was obtained as a colorless solid in 46% yield: mp 122-123° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.28 (t, J=9.0 Hz, 1H), 8.54-8.50 (m, 2H), 8.43-8.41 (m, 1H), 8.36 (d, J=3.0 Hz, 1H), 7.70-7.67 (m, 1H), 7.35-7.29 (m, 2H), 4.45 (d, J=5.7 Hz, 2H), 3.93 (t, J=9.0 Hz, 2H), 3.56 (t, J=9.0 Hz, 2H), 3.06 (d, J=9.0 Hz, 2H), 0.96-0.85 (m, 1H), 0.48-0.42 (m, 2H), 0.21-0.15 (m, 2H); MS (ES+) m/z 352.2 (M+1).

Sources & evidence

ORD record
ord-c111bfe9fe7b473fb92fc131a8751895
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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