4-Fluorobenzylamine → N-(4-fluorobenzyl)-2-(3-(4-fluorobenzylamino)-2-oxopyrrolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 883164Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.Br[CH:11]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][C:18]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:23])=[C:19]([CH3:21])[N:20]=2)[C:12]1=[O:33]>>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:22]([C:18]2[S:17][C:16]([N:13]3[CH2:14][CH2:15][CH:11]([NH:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:12]3=[O:33])=[N:20][C:19]=2[CH3:21])=[O:23])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 247992342-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

Product 1

HCID 24801671N-(4-fluorobenzyl)-2-(3-(4-fluorobenzylamino)-2-oxopyrrolidin-1-yl)-4-methylthiazole-5-carboxamideYield 85%

Procedure

Following the procedure as described in Example 5, making variation as required to use (4-fluorophenyl)methanamine in place of 2-cyclopropylethanamine to react with 2-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 85% yield: mp 123-124° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.35-7.21 (m, 4H), 7.06-6.92 (m, 4H), 6.07 (t, J=5.6 Hz, 1H), 4.50 (d, J=5.6 Hz, 2H), 4.20 (t, J=5.6 Hz, 1H), 3.97-3.76 (m, 3H), 3.68 (t, J=8.6 Hz, 1H), 2.60 (s, 3H), 2.53-2.37 (m, 1H), 2.11-1.89 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 173.6, 162.3, 162.2, 162.1, 155.2, 152.8, 135.0, 133.7, 129.8, 129.6, 118.8, 115.6, 115.4, 58.5, 51.0, 44.8, 43.3, 27.1, 17.3; MS (ES+) m/z 457.3 (M+1).

Sources & evidence

ORD record: ord-a7d022a8f9674afdb1ed9c645e4dacf4
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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