Benzylamine → HCID 44553448, compound

HRID 714382Notes

Reaction equation

C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH2:14].[F:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]2[CH2:29][CH2:28][N:27]([C:30]3[CH:31]=[C:32]([CH:37]=[CH:38][N:39]=3)[C:33](OC)=[O:34])[C:26]2=[O:40])=[CH:22][CH:21]=1>>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH:14][C:33](=[O:34])[C:32]1[CH:37]=[CH:38][N:39]=[C:30]([N:27]2[CH2:28][CH2:29][N:25]([CH2:24][C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:42][CH:41]=3)[C:26]2=[O:40])[CH:31]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 1235723,4-Difluorobenzylamine

HCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44553448HCID 44553448, compoundYield 34%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 3,4-difluorobenzylamine to react with methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate, N-(3,4-difluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 34% yield: mp 182-183° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.37 (d, J=5.1 Hz, 1H), 7.24-6.99 (m, 9H), 4.55 (d, J=5.7 Hz, 2H), 4.42 (s, 2H), 4.04 (t, J=8.1 Hz, 2H), 3.37 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 157.0, 153.0, 148.4, 142.6, 131.9, 129.9, 129.7, 123.9, 117.6, 117.4, 117.0, 116.8, 116.1, 115.9, 115.6, 108.9, 47.2, 43.1, 41.3, 41.1; MS (ES+) m/z 440.9 (M+1).

Sources & evidence

ORD record: ord-5a58c50c9dad4d32bc5326e7262b68ee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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