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

HRID 714375Notes

Reaction equation

C(N)C1C=CC=CC=1.[CH:9]1([CH2:12][CH2:13][NH2:14])[CH2:11][CH2:10]1.[F:15][C:16]1[CH:38]=[CH:37][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][N:35]=3)[C:29](OC)=[O:30])[C:22]2=[O:36])=[CH:18][CH:17]=1>>[CH:9]1([CH2:12][CH2:13][NH:14][C:29](=[O:30])[C:28]2[CH:33]=[CH:34][N:35]=[C:26]([N:23]3[CH2:24][CH2:25][N:21]([CH2:20][C:19]4[CH:18]=[CH:17][C:16]([F:15])=[CH:38][CH:37]=4)[C:22]3=[O:36])[CH:27]=2)[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 10240761Cyclopropaneethanamine

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

Product 1

HCID 44553280N-(2-cyclopropylethyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamideYield 70%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 2-cyclopropylethanamine to react with methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate, N-(2-cyclopropylethyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 70% yield: mp 123-125° C.; 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.38 (dd, J=5.1, 1.2 Hz, 1H), 7.29-7.24 (m, 2H), 7.05-7.00 (m, 2H), 6.52 (br s, 1H), 4.44 (s, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.55-3.49 (m, 2H), 3.37 (t, J=8.1 Hz, 2H), 1.54-1.47 (m, 2H), 0.77-0.64 (m, 1H), 0.53-0.45 (m, 2H), 0.11-0.02 (m, 2H); MS (ES+) m/z 383.3 (M+1).

Sources & evidence

ORD record: ord-c35cb7584e8a48a4a9f1488fe9d6d06c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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