4-Fluorobenzylamine → HCID 44553615, compound

HRID 714390Notes

Reaction equation

HRID 714390 reaction equation
[F:1][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.[F:25][C:26]1[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:27]=1[CH2:28][N:29]1[CH2:33][CH2:32][N:31]([C:34]2[CH:35]=[C:36]([CH:41]=[CH:42][N:43]=2)[C:37](OC)=[O:38])[C:30]1=[O:44].FC1C=CC(CN)=CC=1>>[F:25][C:26]1[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:27]=1[CH2:28][N:29]1[CH2:33][CH2:32][N:31]([C:34]2[CH:35]=[C:36]([CH:41]=[CH:42][N:43]=2)[C:37]([NH:7][CH2:6][C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)=[O:38])[C:30]1=[O:44]

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247794HCID 58247794, compound

Product 1

HCID 44553615HCID 44553615, compoundYield 55%

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-(2,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate to react with 4-fluorobenzylamine, 2-(3-(2,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide was obtained as a colorless solid in 55% yield: mp 171-173° C.; 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.36 (dd, J=5.1, 0.6 Hz, 1H), 7.56-7.27 (m, 4H), 7.07-6.97 (m, 2H), 6.92-6.74 (m, 3H), 4.58 (d, J=6.0 Hz, 2H), 4.48 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.43 (t, J=8.1 Hz, 2H); MS (ES+) m/z 441.1 (M+1).

Sources & evidence

ORD record
ord-8e3420064ae34e60b48816b3257dd6b2
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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