3,4-Difluorobenzylamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(3,4-difluorobenzyl)isonicotinamide

HRID 714380Notes

Reaction equation

HRID 714380 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.[F:45][C:46]1[CH:47]=[C:48]([CH:51]=[CH:52][C:53]=1[F:54])[CH2:49][NH2:50]>>[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:50][CH2:49][C:48]3[CH:51]=[CH:52][C:53]([F:54])=[C:46]([F:45])[CH:47]=3)=[O:17])[C:8]2=[O:22])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 1235723,4-DifluorobenzylamineHCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445532852-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(3,4-difluorobenzyl)isonicotinamideYield 49%

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 3,4-difluorobenzylamine, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(3,4-difluorobenzyl)isonicotinamide was obtained as a colorless solid in 49% yield: mp 134-136° C.; 1H NMR (300 MHz, CDCl3) δ 8.54 (s, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.41-7.39 (m, 1H), 7.17-7.00 (m, 4H), 4.54 (d, J=6.0 Hz, 2H), 4.07 (t, J=8.1 Hz, 2H), 3.60 (t, J=8.1 Hz, 2H), 3.14 (d, J=7.2 Hz, 2H), 1.00-0.87 (m, 1H), 0.58-0.52 (m, 2H), 0.24-0.19 (m, 2H); MS (ES+) m/z 387.3 (M+1).

Sources & evidence

ORD record
ord-72756c364e0c4b70a2c97efd236e1c38
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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