Benzylamine → N-(cyclopropylmethyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide

HRID 714373Notes

Reaction equation

HRID 714373 reaction equation
C(N)C1C=CC=CC=1.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.[F:14][C:15]1[CH:37]=[CH:36][C:18]([CH2:19][N:20]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[C:27]([CH:32]=[CH:33][N:34]=3)[C:28](OC)=[O:29])[C:21]2=[O:35])=[CH:17][CH:16]=1>>[CH:9]1([CH2:12][NH:13][C:28](=[O:29])[C:27]2[CH:32]=[CH:33][N:34]=[C:25]([N:22]3[CH2:23][CH2:24][N:20]([CH2:19][C:18]4[CH:17]=[CH:16][C:15]([F:14])=[CH:37][CH:36]=4)[C:21]3=[O:35])[CH:26]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 75646CyclopropanemethanamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 44553109N-(cyclopropylmethyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamideYield 54%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with cyclopropylmethanamine to react with methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate, N-(cyclopropylmethyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 54% yield: mp 135-137° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.38 (d, J=5.1 Hz, 1H), 7.29-7.24 (m, 2H), 7.05-6.99 (m, 2H), 6.50 (br s, 1H), 4.45 (s, 2H), 4.07-4.02 (m, 2H), 3.46-3.26 (m, 4H), 1.08-0.97 (m, 1H), 0.56-0.50 (m, 2H), 0.28-0.23 (m, 2H); MS (ES+) m/z 369.2 (M+1).

Sources & evidence

ORD record
ord-ba7145ec3e0043fea610137c0fd4a87b
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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